Labex-csc.unistra.fr

JSPS Bilateral Joint Research Seminar Interdisciplinary Seminar for Innovative Organic Chemistry Dec. 1, 2014  Dec. 3, 2014 The University of Strasbourg Institut de Science et d'Ingénierie Supramoléculaires 1:15 - 2:00 PM Registration and Poster installation 2:00 - 2:10 PM Opening Remarks: Mir Wais Hosseini and Atsuko Hisada Session 1: Transition Metal Catalysis
Chair – Seiji Suga 2:10 - 3:00 PM Pierre Braunstein (Strasbourg) 3:05 - 3:55 PM Dominique Armspach (Strasbourg) 3:55 - 4:15 PM Coffee Break Chair – Jean-Marc Planeix 4:15 - 5:05 PM Yasushi Nishihara (Okayama) 5:10 - 6:00 PM Anny Jutand (ENS Paris) 6:00 - 7:40 PM Poster Session Session 2: Organocatalysis
Chair – Yutaka Takaguchi 1:45 - 2:35 PM Joseph Moran (Strasbourg) 2:40 - 3:30 PM Hiroki Mandai (Okayama) 3:30 - 3:50 PM Coffee Break Chair – Mir Wais Hosseini 3:50 - 4:40 PM Stéphane Bellemin-Laponnaz (Strasbourg) 4:45 - 5:35 PM Seiji Suga (Okayama) Dec. 3, Wednesday Session 3: Supramolecular & Material Chemistry
Chair – Joseph Moran 1:45 - 2:35 PM Tomoyuki Tajima (Okayama) 2:40 - 3:30 PM Wais Hosseini (Strasbourg) 3:30 - 3:50 PM Coffee Break Chair – Yasushi Nishihara 3:50 - 4:40 PM Yutaka Takaguchi (Okayama) 4:45 - 5:35 PM Eric Monflier (Artois) 5:35 - 5:40 PM Closing Remarks Seiji Suga Palladium-catalyzed cascade cyclizations : An original access to Sulfur
Heterocycles
Thomas Castanheiro, Morgan Donnard, Mihaela Gulea and Jean Suffert Laboratoire d'Innovation Thérapeutique, UMR 7200 CNRS-Unistra, Faculté de Pharmacie, Université de Strasbourg, 74 Route du Rhin, Illkirch, France Enantioselective Steglich Rearrangement of Oxindole by a Chiral DMAP
Derivatives: Hydrogen Bonding Strongly Affects Activity and Selectivity
Fujii, a Hiroki Mandai*a Toshinobu Korenagab and Seiji Suga*a aDivision of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, bDepartment of Chemistry and Bioengineering, Faculty of Engineering, Iwate University Ammonium Complexation by 18C6 in Heterogeneous Solutions: a
Simulation
Gael Benay and Georges Wipff Laboratoire MSM, UMR7177,1 rue B. Pascal, 67 000 Strasbourg France Kinetic Resolution of Amines by the Asymmetric Counteranion-Directed
Catalysis
Kengo Goto, Hiroki Mandai*, and Seiji Suga* Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology,Okayama University Molecular tectonics: from crystals to "crystals of crystals"
Adolf,a Sylvie Ferlay,a Nathalie Kyritsakas a and Mir Wais Hosseini a aMolecular Tectonic Laboratory, UMR UDS-CNRS 7140, Université de Strasbourg, Institut Le Bel, 4, rue Blaise Pascal, F-67000 Strasbourg, France. Preparation of [4]CPDT via a Square-Shaped Tetranuclear Platinum
Yasuhiro Okuda, and Yasushi Nishihara* Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Technology, Okayama University Nitro-Assisted Brønsted Acid Catalysis: Application to a Challenging
Catalytic
Azidation
Marian Dryzhakov Malik Hellal, Eléna Wolf and Joseph Moran* Laboratory of Chemical Catalysis, ISIS& icFRC, Université de Strasbourg & 8 allée Gaspard Monge, 67000 Strasbourg, France Synthesis and Self-Assembly of a New [60]Fullerene-Pentacene
Monoadduct
Takuya Nishihama, Tomoyuki Tajima, and Yutaka Takaguchi* Graduate School of Environmental and Life Science, Okayama University Supramolecular Luminescent Lanthanide Dimers for Fluoride
Sequestering and Sensing
Tao Liu, Aline Nonat, Franck Camerel, Raphael Tripier, Carlos Platas-Iglesias, and Loïc J. Charbonnière* Laboratory of Molecular Engineering Applied to Analysis, CNRS, IPHC, Synthesis, Self-Assembly, and Semiconducting Property
of Soluble Hexathiopentacene Derivative
Hitoshi Shirai, Tomoyuki Tajima, and Yutaka Takaguchi* Division Sustainability of Resources, Graduate School of Environmental and Life Science, Okayama University Rational design for "grid of grids"
Jan Holub, Adrian-Mihail Stadler, Jean-Marie Lehn ISIS, 8 allée Gaspard Monge, 67083 Strasbourg, France Organocatalyzed and Uncatalyzed C=C/C=C and C=C/C=N Exchange
Processes between Knoevenagel and Imine Compounds in Dynamic
Covalent
Chemistry
Sirinan Kulchat, Kamel Meguellati, Jean-Marie Lehn ISIS, 8 allée Gaspard Monge, 67083 Strasbourg, France An In Situ Combinatorial Approach to Boron Lewis Acid Catalysis
Eléna Wolf, Florian C. Falk, Malik Hellal and Joseph Moran* Laboratory of Chemical Catalysis, ISIS, University of Strasbourg Magnetic field-induced supramolecular self-assembly
Marichez1, A. Sato1, I. de Feijter2, P. Besenius2, E. W. Meijer2, T. M. 1Laboratoire des systèmes complexes hors-équilibre (ISIS), Strasbourg 2Institute for complex molecular systems (TU/e), Eindhoven LbL multi-particle coating: Toward smart textiles
M. Twardoch, D. Martel, O. Felix, G. Decher, N. Keller, M. Motay, V. Keller Centre National de la Recherche Scientifique, Institut Charles Sadron

Pierre Braunstein
Institute of Chemistry (UMR 7177 CNRS) - University of Strasbourg [email protected] Pierre Braunstein obtained his Dr. Ing. Degree and « State Doctorate » from the
Université Louis Pasteur in Strasbourg. After post-doctoral stays at University College London with R. S. Nyholm and R. J. H. Clark and at the TU Munich (Germany) as a Humboldt Fellow with E. O. Fischer (Nobel Laureate), he returned to Strasbourg where he became Director of Research with the CNRS and Head of the Coordination Chemistry Laboratory (Institute of Chemistry, UMR 7177 CNRS) of the University of Strasbourg. His main research interests deal with the inorganic and organometallic chemistry of the transition and main group elements where he has (co)authored over 500 scientific publications and review articles. He has received numerous national and international awards (including the International Award of the Japan Society of Coordination Chemistry in 2013) and is member i.a. of the french Académie of Sciences and the German National Academy of Sciences Leopoldina. He has been recently featured in Angewandte Chemie Selected Reviews 1. (a) Zhang, S.; Pattacini, R.; Braunstein, P. in Organometallic Chemistry: Recent Advances, A. J. L. Pombeiro (Ed.), Elsevier, Chapter 14, pp. 185-198, 2014. (b) Fliedel, C.; Braunstein, P. J. Organomet. Chem. 2014, 751, 286. (c) Boudier, A. ; Breuil, P.-A.
R. ; Magna, L.; Olivier-Bourbigou, H.; Braunstein, P. Chem. Commun., 2014, 50, 1398
(d) Braunstein, P. Chem. Rev. 2006, 106, 134. (e) Speiser, F.; Braunstein, P.; Saussine,
L. Acc. Chem. Res. 2005, 38, 784.
Reactivity Resulting from Heterodonor Ligands in Mono- and Polynuclear Complexes
Pierre BRAUNSTEIN Institut de Chimie (UMR 7177 CNRS), University of Strasbourg, 4 rue Blaise Pascal, 67081 Strasbourg, France E-mail: [email protected] Combining chemically-different donor groups within the same ligand allows access to metal complexes of diverse nuclearities endowed with structural or chemical properties often very different from those of complexes containing identical donor groups.[1] Such systems are ideal candidates for the study of the chemoselectivity of their coordination to metal centres. We will examine the impact of ligands containing a phosphorous or a NHC donor group associated with another function on the synthesis and structure of organometallic/coordination complexes and the reactivity and catalytic applications of the latter.[2-11] [1] For recent reviews, see e.g. (a) Speiser, F.; Braunstein, P.; Saussine, L. Acc. Chem. Res. 2005, 38, 784. (b) Braunstein, P. Chem. Rev. 2006, 106, 134. (c) Fliedel, C.;
Braunstein, P. J. Organomet. Chem. 2014, 751, 286.
[2] Liu, X.; Braunstein, P. Inorg. Chem. 2013, 52, 7367.
[3] Rosa, V. ; Fliedel, C. ; Ghisolfi, A.; Pattacini, R.; Aviles, T.; Braunstein, P. Dalton Trans. 2013, 42, 12019.
[4] Ghisolfi, A.; Fliedel, C.; Rosa, V.; Pattacini, R.; Thibon, A.; Monakhov, K. Yu.; Braunstein, P. Chem. Asian J. 2013, 8, 1795.
[5] Liu, P.; Wesolek, M.; Danopoulos, A. A.; Braunstein, P. Organometallics, 2013,
32, 6286. [6] Ai, P. ; Danopoulos, A. A.; Braunstein, P. ; Monakhov, K. Yu. Chem. Commun. 2014, 50, 103.
[7] Massard, A.; Rogez, G.; Braunstein, P. Dalton Trans. 2014, 43, 42.
[8] Ai, P.; Danopoulos, A. A.; Braunstein, P. Dalton Trans. 2014, 43, 1957.
[9] Fliedel, C.; Faramarzi, V.; Rosa, V.; Doudin, B.; Braunstein, P. Chem. Eur. J. 2014, 20, 1263.
[10] Hameury, S.; de Frémont, P.; Breuil, P.-A. R.; Olivier-Bourbigou, H.; Braunstein, P., Dalton Trans. 2014, 43, 4700; Inorg. Chem. 2014, 53, 5189.

Dominique Armspach
Laboratoire de Chimie Organique Moléculaire et Catalyse Institut de Chimie de Strasbourg (UMR 7177), Université de Strasbourg Phone: +33(0)368851621 [email protected] Dominique Armspach was born in Mulhouse (France) in 1965. As a graduate of the Ecole Nationale Supérieure de Chimie de Mulhouse, he joined Professor J. F. Stoddart's group at the University of Birmingham (GB) in 1990 where he completed his Ph.D. in 1994. He then spent three years at the University of Basle (Switzerland) as a postdoctoral fellow and teaching assistant in Professor E. C. Constable's laboratory before becoming Lecturer in Organic Chemistry in Strasbourg in 1996. In 2003, he was habilitated to conduct independent research (HDR) by the Université Louis Pasteur in Strasbourg and was promoted Professor of Organic Chemistry four years later at the University of Strasbourg. His present interests focus on synthetic methodology, supramolecular chemistry, organometallic chemistry and catalysis associated with molecular receptors. Selected Reviews and Papers 1. A Cavity-Shaped Diphosphane Displaying "Oschelating" Behavior. R. Gramage-Doria, D. Armspach, Dominique Matt, L. Toupet, Angew. Chem. Int. Ed. 2011, 50, 1554-1559.
2. TRANSDIP: A trans-Chelating Ligand Tailor-Made for Probing Unusual Pd0 and PdII Intermediates. R. Gramage-Doria, D. Armspach, D. Matt, L. Toupet, Chem. Eur. J. 2012, 10813-10816.
3. Confining Phosphanes Derived from Cyclodextrins for Efficient Regio and Enantioselective Hydroformylation. M. Jouffroy, R. Gramage-Doria, D. Armspach, D. Sémeril, W. Oberhauser, D. Matt, L. Toupet, Angew. Chem. Int. Ed. 2014, 53, 3937-3940.

Phosphinocyclodextrins as confinement ligands for late transition metal centres
Dominique ARMSPACH Laboratoire de Chimie Organique Moléculaire et Catalyse Institut de Chimie de Strasbourg (UMR 7177), Université de Strasbourg 1, rue Blaise Pascal 67008 STRASBOURG Cedex Phone: +33(0)368851621 [email protected] Confinement is one of the most defining features in enzymes, Nature's own catalysts. By combining P(III) coordinating units with cyclodextrin-based receptors, we were able to synthesise ligands that force late transition metals to stay within a cyclodextrin cavity so as to mimic the confinement of the active site that is observed in metalloenzymes.1 The chiral environment that surrounds the metal centre is responsible for unusual coordination chemistry, unique supramolecular interactions and highly selective catalytic reactions of industrial importance taking place within the cyclodextrin hollow. Metal confinement M = late transition metal
1. Metallated Cavitands (Calixarenes, Resorcinarenes, Cyclodextrins) with Internal Coordination Sites. R. Gramage-Doria, D. Armspach, D. Matt, Coord. Chem. Rev. 2013, 257, 776-816.

Yasushi Nishihara
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan Education B Sc: 1992, Faculty of Science, Hiroshima University M Sc: 1994, Graduate School of Science, Hiroshima University Ph D: 1997, The Graduate University for Advanced Studies
Professional Experience
1994.10-2004.3
Assistant Professor, Chemical Resources Laboratory, Tokyo Institute of Technology 2004.3-2010.3 Associate Professor, Okayama University Professor, Okayama University Awards 1. Young Top Researcher, Okayama University (2007) 2. Chemical Society of Japan Presentation Award 2008 for Industries (2008) 3. Incentive Award in Synthetic Organic Chemistry, Japan (2009) 4. Incentive Culture Award in Okayama Prefecture, Japan (2010) Selected Reviews and Papers 1. Nishihara, Y.; Okada, Y.; Jiao, J.; Suetsugu, M.; Lan, M.-T.; Kinoshita, M.; Iwasaki, M.; Takagi, K. Angew. Chem. Int. Ed. 2011, 50, 8660.
2. Nishihara, Y.; Miyasaka, M.; Okamoto, M.; Takahashi, H.; Inoue, E.; Tanemura, K.; Takagi, K. J. Am. Chem. Soc. 2007, 129, 12634.
Synthesis of Substituted Picenes and Their Derivatives and
Their Application to Field-Effect Transistor Devices
Yasushi Nishihara Graduate School of Natural Science and Technology, Okayama University, Okayama 700-8530, Japan Japan Science and Technology Agency (JST), ACT-C, Kawaguchi, Saitama 332-0012, Japan Organic thin-film transistors (OTFTs) with [n]phenacenes have attracted much attention because of their superior organic field-effect transistors (OFETs) characteristics. The [5]phenacene (picene) and [6]phenacene (fulminene)-based OTFT have been fabricated and the field-effect mobility, μFET, reached the value as high as 3.2 and 3.7 cm2/Vs under O2 atmosphere, respectively. From the synthetic point of view, there are several critical drawbacks in the reported synthetic methods for [n]phenacenes. Therefore, a simple and convenient strategy for the synthesis of various substituted [n]phenacenes is highly desirable in order to promote further investigations into the ideal OFETs, which may be solution-processed and exhibit high carrier mobility and solubility in common organic solvents. Previously, we have reported the synthesis of picene,1,2 fulminene,3 and phenanthro[1,2-b:8,7-b']dithiophene (PDT)4 through cross-coupling reaction of polyhalobenzene with (Z)-alkenylboron compounds and sequential double cyclization via C-H bond activation (Figure 1). However, this synthetic method is not suitable for a large-scale synthesis due to a tedious isolation of stereoisomers of precursor and a low overall yield. Chart 1. Structures of [5]- and [6]phenacenes and PDT
In this presentation, we disclose a new synthetic route to PDF and structure-property relationships in Cn-PDT-based OFETs.5 First, PDT 6 was synthesized through the palladium-catalyzed Suzuki–Miyaura
or Negishi couplings of 2-thienylboronic acid 1 or the corresponding zinc compound 4
with 1,4-dibromobenzene 2 followed by epoxidation/Lewis-acid-catalyzed
Friedel-Crafts-type intramolecular cyclization sequences. Furthermore, dibromination
of 6 and sequential Suzuki–Miyaura coupling with alkylboranes, derived from 9-BBN
and terminal alkenes, gave Cn-PDTs 8a-8f in 69-80% yields (Scheme 1).
Scheme 1. Synthetic procedure of PDT and Cn-PDTs
Next, OFET devices were fabricated by using 8a-8f on Si/SiO2 substrate, in which
thin films were formed by thermal deposition. As a result, the
2,9-didodecylphenanthro[1,2-b:8,7-b']dithiophene (C12-PDT) thin-film FET displays
superior properties, with μ's as high as 1.4 cm2 V–1 s–1 for the SiO2 gate dielectric and 2.2
cm2 V–1 s–1 for the HfO2 gate dielectric. The average μ values, <μ>'s, reach 1.1(5) and
1.8(6) cm2 V–1 s–1, respectively, for the SiO2 and ZrO2 gate dielectrics.
References
1. Chang, N.; Chen, X.; Nonobe, H.; Okuda, Y.; Mori, H.; Nakajima, K.; Nishihara, Y.
Org. Lett. 2013, 15, 3558.
2. Mori, H.; Chen, X.; Chang, N.; Hamao, S.; Kubozono, Y.; Nakajima, K.; Nishihara, Y. J. Org. Chem. 2014, 79, 4973.
3. Chang, N.; Mori, H.; Chen, X.; Okuda, Y.; Okamoto, T.; Nishihara, Y. Chem. Lett. 2013, 42, 1257.
4. Nishihara, Y.; Kinoshita, M.; Hyodo, K.; Okuda, Y.; Eguchi, R.; Goto, H.; Hamao, S.; Takabayashi, Y.; Kubozono, Y. RSC Adv. 2013, 3, 19341.
5. Hyodo, K.; Nonobe, H.; Nishinaga, S.; Nishihara, Y. Tetrahedron Lett. 2014, 55,
Anny Jutand
Ecole Normale Supérieure, Département de Chimie 24 Rue Lhomond, F-75231 Paris Cedex 5, France Phone: +33144323872 [email protected] Anny Jutand obtained her Master Degree in 1971 at the Ecole Nationale Supérieure de Chimie, Paris VI and the PhD in Chemistry in 1980 at the University Paris XIII (advisor: Professor J. F. Fauvarque), developing palladium/nickel-catalyzed arylation of Grignard reagents and zinc enolates. In 1980-1981, she was a Post-doctoral fellow at the Royal Institute of Technology in Stockholm, Sweden (advisor: Professor B. Åkermark) working on nucleophilic attack of enolates on -allyl palladium and coupling of nucleophiles with cuprates via electrochemical oxidation. In1981-1985, she went back to University Paris XIII as Chargé de Recherche (equivalent to Associate Professor) at CNRS (Centre National de la Recherche Scientifique) where she developed nickel-catalyzed electrosynthesis of anti-inflammatory agents (ibuprofen, naproxen…). In 1985, she joined Dr. C. Amatore' s group at the Ecole Normale Superieure in Paris. She became Research Director 2nd class at CNRS (a position equivalent to full Professor) in 1992 and then Director of Research 1st class at CNRS in 2005. She is Emeritus since Oct 2013. Current Research Interests since 1985 :
* Mechanistic studies on transition metal-catalyzed reactions (Pd, Ni, Cu, Fe, Ru, Rh) * Activation of organic molecules by transition metal complexes and by electron transfer. Synthetic development and mechanism Author of 169 publications in international journals, 7 industrial patents, 11 articles or
chapters in collective books, 115 conferences or seminars - H factor: 48
1. Award 2003 of the Organic Chemistry Division of the French Chemical Society
2. Grand Prix d'Etat of the French Academy of Sciences, 2008
3. Prix Achille Le Bel (French Chemical Society) 2013
Selected Reviews and Papers
1. Acc. Chem. Res. 2000, 33, 314-321.
2. Eur. J. Inorg. Chem. 2003, 2017-2040.
3. Chem. Rev. 2008, 108, 2300-2347.
Recent insights into the mechanism of transition metal-catalyzed reactions
Anny Jutand Ecole Normale Supérieure, Département de Chimie 24 Rue Lhomond, F-75231 Paris Cedex 5, France [email protected] Transition metal catalyzed reactions proceed via catalytic cycles which are a succession of chemical steps involving catalytic species whose metal exhibits different oxidation states. Most organometallic complexes are electroactive. Consequently, they can be detected and characterized by their reduction (or oxidation) potential by means of electrochemical techniques. Moreover, since their reduction (or oxidation) currents are proportional to their concentration, the reactivity of organometallic species with organic substrates can be monitored by electrochemistry and the rate constants (or equilibrium constants) determined.1 It is thus possible to investigate the mechanism of all steps of a catalytic cycle, to determine factors that control the efficiency of a catalytic reaction, to understand how and why a catalytic reaction works, so that to increase its efficiency in terms of turn-over and selectivity. The mechanisms of palladium2, copper3 and ruthenium4–catalyzed reactions will be References
1. A. Jutand, Chem. Rev. 108, 2008, 2300.
2. C. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J. 2011, 17, 2492; Angew. Chem. Int.
Ed. 2012, 51, 1379; Chem. Eur. J. 2012, 18, 6616. Chem. Eur. J. 2013, 19, 10082.
3. G. Franc, Q. Cacciuttolo, G. Lefèvre, C. Adamo, I. Ciofini, A. Jutand, ChemCatChem 2011, 3, 305; Organometallics, 2012, 31, 914.
4. E. Ferrer Flegeau, C. Bruneau, P. H. Dixneuf, A. Jutand, J. Am. Chem. Soc. 2011,
133, 10161. I. Fabre, N. von Wolff, G. Le Duc, E. Ferrer Flegeau, C. Bruneau, P. H. Dixneuf, A. Jutand, Chem. Eur. J. 2013, 19, 7595.

Joseph Moran
ISIS & icFRC, Université de Strasbourg & CNRS, 8 allée Gaspard Monge, 67000 Strasbourg, France Phone: +33-0368855202 [email protected] Joseph Moran is an Assistant Professor of Chemistry at the University of Strasbourg's Institute of Supramolecular Science and Engineering (ISIS) and is the director of the Laboratory of Chemical Catalysis since September 2012. He received his Ph.D. in 2009 from the University of Ottawa (Canada) under the direction of Prof. André M. Beauchemin. After a brief stay as a visiting scientist at the National Research Council of Canada under the direction of John P. Pezacki, in 2010 he moved to the University of Texas at Austin to take up an NSERC Postdoctoral Fellowship under the direction of Prof. Michael J. Krische from 2010. Marie Curie CIG (2013), Thieme Chemistry Journal Award (2013), NSERC Postdoctoral Fellowship (2010), Boehringer Ingelheim Graduate Research Award in Organic Chemistry (2008), NSERC Doctoral Scholarship (2006). Selected Reviews and Papers 1. Review: Pure Appl. Chem. 2012, 84, 1729-1739.
2. J. Am. Chem. Soc. 2011, 133, 20100-20103.
3. J. Am. Chem. Soc. 2011, 133, 18618-18621.
4. Nature Chem. 2011, 3, 287-290.
Harnessing Complexity in Catalysis: From Supramolecular
Preorganization to Combinatorial Strategies
Joseph Moran ISIS & icFRC, Université de Strasbourg & CNRS 8 allée Gaspard Monge, 67000 Strasbourg, France [email protected]. The spatial pre-organization of multiple hydrogen bond donor sites within the molecular framework of enzymes is a major reason why biological catalysts produce dramatic rate acceleration with impressive selectivity. Supramolecular approaches to the pre-organization of multiple hydrogen bond catalysts can also lead to much higher reaction rates while providing a modular and easily tunable catalyst system without the need for intensive synthetic efforts. The first half of the talk will describe our efforts to develop and exploit template co-catalysts for the supramolecular preorganization of multiple hydrogen bond catalysts. Catalytic reaction discovery and development is a multidimensional problem that often requires extensive experimentation to obtain a lead result. In a representative scenario, metal, ligand, solvent, acid/base additive and temperature may all be critical to a desired reaction, making catalytic reaction development a bit like finding a needle in a haystack. The second half of the talk will describe our efforts to develop a multidimensional combinatorial approach to the discovery of catalyst systems that are generated in situ from complex mixtures, a technique that we hope can dramatically reduce the number of reactions required to obtain a lead result. 1. Org. Biomol. Chem. 2014, 12, 5990-5994.

Hiroki Mandai
Division of Chemistry and Biotechnology Graduate School of Natural Science and Technology, Okayama University Phone: +81-86-251-8604, FAX: +81-86-251-8082
Hiroki Mandai obtained his Ph. D degree in 2006 from Tokyo University of Science
under the direction of Professor Teruaki Mukaiyama, focusing on the development of
stereoselective glycosylation reaction. He then joined the group of Amir H. Hoveyda at
Boston College as postdoctoral fellow from 2006 to 2008. He became assistant
professor at Okayama University from October 2008. His current research interests
include development of enantioselective reactions with chiral nucleophilic catalyst, and
synthesis of biologically important molecules.
Awards
Lectureship Award of the 89th Annual Meeting of the Chemical Society of Japan
(2009), Science and Technology Award of Okayama Foundation of Science and
Technology (2009), KANEKA CORPORATION Award in Synthetic Organic
Chemistry, Japan (2009).
Selected Reviews and Papers
1. Mandai, H.; Murota, K.; Mitsudo, K.; Suga, S. Org. Lett. 2012, 14, 3486.
2. Mandai, H.; Shimowaki, K.; Mitsudo, K.; Suga, S. Asian J. Org. Chem. 2014, 3, 437.
3. Mandai, H.; Omori, K.; Yamamoto, D.; Tsumura, T.; Murota, K.; Yamamoto, S.; Mitsudo,
K.; Ibaragi, S.; Sasaki, A.; Maeda, H.; Takashiba, S.; Suga, S. Biorg. Med. Chem. 2014, 22,
5338.
Development of Chiral Nucleophilic Catalysts
Hiroki Mandai* Division of Chemistry and Biotechnology Graduate School of Natural Science and Technology, Okayama University 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan Over the past two decades, the development of chiral nucleophilic catalysts has become one of the most important fields in the enantioselective catalysis.1 Chiral catalysts with N,N-4-dimethylaminopyridine (DMAP) or 4-pyrrolidinopyridine (PPY) scaffolds have been widely studied in response to the pioneering studies by Vedejs2 and Fu,3 and have been used in various enantioselective transformations, such as the kinetic resolution of racemic alcohols or amines, desymmetrization of meso-compounds, Steglich rearrangements, and many others. Although considerable effort has been made to explore a variety of chiral DMAP and PPY derivatives, these catalysts often required the optical resolution of a racemic intermediate or catalyst during catalyst synthesis. Thus, highly active and enantioselective chiral nucleophilic catalysts, which can be synthesized from both readily available enantiomers of a chiral source and which do not require optical resolution during catalyst synthesis, are strongly desired. Against this background, we designed and synthesize a new class of chiral DMAP derivatives based on two strategies: (1) the use of diastereoselective Ugi reaction,4 and (2) the use of (S)-1,1́-bi-2-naphtol (BINOL) as chiral source. This lecture will be focused on the development of chiral nucleophilic catalysts and application to enantioselective transformations. References 1. (a) Wurz, R. P. Chem. Rev. 2007, 107, 5570; (b) Müller, C. E.; Schreiner, P. R. Angew.
Chem. Int. Ed. 2011, 50, 6012; (c) Pellissier, H. Adv. Synth. Catal. 2011, 353, 1613.
Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809.
Fu, G. C. Acc. Chem. Res. 2000, 33, 412.
(a) Mandai, H.; Irie, S.; Mitsudo, K.; Suga, S. Molecules 2011, 16, 8815; (b) Mandai,
H.; Irie, S.; Akehi, M.; Yuri, K.; Yoden, M.; Mitsudo, K.; Suga, S. Heterocycles 2013,

Stéphane Bellemin-Laponnaz
Insititut de Physique et Chimie des Matériaux de Strasbourg CNRS-Université de Strasbourg Phone +33-(0)388-107-166 [email protected] Stéphane Bellemin-Laponnaz studied chemistry at the Université Joseph Fourier (Grenoble) and the Université Louis Pasteur (Strasbourg). He obtained his doctorate in 1998 under the direction of Prof. John A. Osborn and Dr J. P. Le Ny working in the field of homogeneous catalysis. He then joined the group of Prof. Gregory C. Fu at the Massachusetts Institute of Technology (Cambridge, MA) as a post-doctoral fellow working on asymmetric catalysis. In late 2000, he joined the group of Prof. Lutz H. Gade at the Université de Strasbourg as an associate researcher CNRS and moved in 2010 to the Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS) as Directeur de recherche CNRS. His research interests are in the fields of organometallic chemistry, coordination chemistry, catalysis and medicinal chemistry. 1. CNRS, Bronze Medal 2005 2. French Chemical Society, Coordination Chemistry Division Award 2009 3. Swiss Chemical Society, Sandmeyer Award 2013 4. USIAS, Fellow 2013 1. Angew. Chem. Int. Ed. 2008, 47, 4546; 2009, 48, 1609; 2010, 49, 2198.
2. Chem. Commun. 2011, 47, 5864; 2012, 2213.
3. Organometallics 2010, 29, 1191; 2012, 31, 7618; 2013, 32, 2736; 2014, 33,
4. Chem. Rev. 2011, 111, 2705; 2014, 114, 8747.
Catalytic Performance And Recycling of Oxazoline-Based Catalysts
Maria Torres,1 Manuela Gaab,1,2 Carole Foltz-César,1,2 Lutz H. Gade,2 Stéphane Bellemin-Laponnaz*,1 1IPCMS CNRS-Université de Strasbourg, STRASBOURG, France, 2 Anorganisch-Chemisches Institut, Universität Heidelberg, HEIDELBERG, Germany Asymmetric catalysis constitutes a privileged approach for the production of enantiopure compounds. Today a large number of chiral catalytic processes may deliver products with very high enantiomeric excesses (and yields) and some systems have been applied on an industrial scale. However, homogeneous asymmetric catalytic systems frequently exhibit relatively low activity for a large-scale application and they also suffer from two drawbacks: (i) possible product contamination: in particular, metal contamination in active pharmaceutical ingredients or fine chemicals is a serious concern and the remaining metal traces must be reduced to ppm amount in the final products and, (ii) inability to reuse the homogeneous catalyst. Due to the high cost of both the chiral ligand and the metal, it is highly desirable to develop catalytic systems that are active at a very low catalytic level and/or that allow an easy separation from reaction mixture and efficient recycling. In the first part of this lecture, highly symmetric oxazoline-based catalysts will be described. In particular, we will present how the concept of stereoelectronic hemilabillity allows a decrease of the catalyst loading.1 In the second part of this lecture, recent progress in the development of reusable asymmetric catalysts will be discussed. Two strategies have been investigated: (i) covalent attachment to carbosilane dendrimers2 and (ii) conception of polytopic ligands for the development self-supported systems.3 1. a) Gade, L. H.; Bellemin-Laponnaz, S. Chem. Eur. J. 2008, 14, 4152; b) Foltz, C.;
Stecker, B.; Marconi, G.; Bellemin-Laponnaz, S.; Wadepohl, H.; Gade L. H. Chem. Eur. J. 2007, 13, 9912; c) Foltz, C.; Enders, M; Bellemin-Laponnaz, S.; Wadepohl,
H.; Gade, L. H. Chem. Eur. J. 2007, 13, 5994.
2. Gaab, M.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Eur. J. 2009, 15, 5450.
3. a) Torres, M.; Heinrich, B.; Miqueu, K.; Bellemin-Laponnaz, S.; Eur. J. Inorg. Chem. 2012, 3384; b) Torres, M.; Maisse-François, A.; Bellemin-Laponnaz, S.
ChemCatChem 2013, 5, 3078; c) Torres, M.; Nano, A.; Maisse-François, A.;
Bellemin-Laponnaz, S. New J. Chem. 2014 in press.
Seiji Suga
Division of Chemistry and Biotechnology Graduate School of Natural Science and Technology, Okayama University Phone: +81-86-251-8081 FAX: +81-86-251-8081 [email protected] Prof. Seiji Suga educated in organic chemistry at Nagoya University under the direction of Prof. Ryoji Noyori. After earning his PhD degree in 1995, he became a postdoctoral fellow (JSPS Postdoctoral Fellowships for Research Abroad) with Prof. Sir Jack E. Baldwin at Oxford University. Then he joined the group of Jun-ichi Yoshida at Kyoto University as Instructor in 1996, and was promoted to Lecture (1999) and Associate Professor (2004). In 2008 he was appointed Professor of Okayama University. His research interest has been focused on electron-transfer reactions of organic compounds and reaction processes development. Fujisawa Pharmaceutical Co. Award in Synthetic Organic Chemistry, Japan (1999), Incentive Award in Synthetic Organic Chemistry, Japan (2004), Incentive Award in Organic Electron-transfer Chemistry, Japan (2004), BCSJ Award (2005), Nagase Foundation Award (2012) 1. Suga, S.; Nishida, T.; Yamada, D.; Nagaki, A.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 14338.
2. Matsumoto, K.; Fujie, S.; Ueoka, K.; Suga, S.; Yoshida, J. Angew. Chem. Int. Ed. 2008, 47,
3. Suga, S.; Yamada, D.; Yoshida, J. Chem. Lett. 2010, 39, 404.
4. Mitsudo, K.; Shimohara, S.; Mizoguchi, J.; Mandai, H.; Suga, S. Org.Lett. 2012, 14, 2702.
Electrochemically Generated Carbocations
for Stereoselective Synthesis and Catalytic Reactions
Seiji Suga* Division of Chemistry and Biotechnology Graduate School of Natural Science and Technology, Okayama University 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan [email protected] Electric process in organic synthesis is advantageous because of its versatility and environmental benefit. It is also noteworthy that highly reactive species such as synthetically useful carbocations can easily be generated by the simple electron-transfer The first topic will be diastereoselective synthesis of di-substituted piperidine derivatives accomplished by the reaction of N-acyliminium ions prepared by the Indirect Cation Pool Method.2 The highly reactive N-acyliminium ions having a piperidine skeleton with a substituent can be generated and accumulated from the corresponding thioaminals by the treatment of electrochemically generated ArS(ArSSAr)+ pool. The nucleophilic addition of carbon nucleophiles gave rise to the formation of the corresponding of di-substituted piperidine derivatives in a highly-stereoselective manner. Organocations such as trityl cation effectively promote Mukaiyama-Aldol reactions.3 The interesting reactions involving carbocation chemistry prompted us to develop a redox-switchable reaction involving entirely organic compounds, because the redox-switchable catalysis is an emerging research field that seeks to regulate chemical reactions by the simple reduction-oxidation manipulation. The second topic in this presentation will be the catalytic reaction promoted by the electrochemically generated carbocations. When the solution of an aldehyde, enol silyl ether and a precursor of organo-dication4 were subjected to the electrochemical oxidation, the aldol reaction smoothly started. Subsequent electrochemical reduction of the solution brought the reaction to a stop. (1) J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2650. (2) S. Suga, K. Matsumoto, K. Ueoka, J.
Yoshida, J. Am. Chem. Soc. 2006, 128, 7710. (3) T. Mukaiyama, S. Kobayashi, M. Murakami, Chem.
Lett. 1984, 1759. J. Bah, J. Franzén, Chem.-Eur. J. 2014, 20, 1066 (4) M. Okajima, S. Suga, K. Itami,
J. Yoshida, J. Am. Chem. Soc. 2005, 127, 6930.
Tomoyuki Tajima
Graduate School of Environmental and Life Science, Okayama University Phone & Fax: +81-86-251-8898 Tomoyuki Tajima received his Ph. D. (2005) degree from Kyoto University under the supervision of Prof. Norihiro Tokitoh. He was granted a Fellowship of the Japan Society for the Promotion of Science (JSPS) for Young Scientists (2004-2005). In 2006, he moved to Saitama University of Science as a research associate of Prof. Masaichi Saito group. In 2007, he joined the Research Center for Materials Science (RCMS), Prof. Kazuyuki Tatsumi group, at Nagoya University as a researcher. He moved back to Kyoto University as an assistant professor in 2008. Then, he appointed as a senior assistant professor at Okayama University in 2009. Selected Reviews and Paper 1. Photosensitized hydrogen evolution from water using single-walled carbon
nanotube/fullerodendron/Pt(II) coaxial nanohybrids, Y. Sasada, T. Tajima, T. Wada, T.
Uchida, M. Nishi, T. Ohkubo and Y. Takaguchi, New Journal of Chemistry 2013, 37,
4214-4219.
2. Fabrication of novel core-shell microspheres consisting of single-walled carbon
nanotubes and CaCO3 through biomimetic mineralization, T. Tajima, A. Tsutsui, T.
Fujii, J. Takada and Y. Takaguchi, Polymer Journal 2012, 44, 620-624.
3. Synthesis and characterization of 2,3,9,10-tetradendronized pentacene, T. Tajima, A. Yamakawa, K. Fukuda, Y. Hayashi, M. Nakano, and Y. Takaguchi, Chemistry Letters 2012, 41, 1622-1624.
4. Photoreactive molecule incorporated within dendritic architecture, Y. Takaguchi
and T. Tajima, Journal of Synthetic Organic Chemistry Japan 2011, 69, 705-714.
Synthesis and Properties of (Terthiophene)4-poly(amidoamine)-C60 pentad
Tomoyuki Tajima*, Takuya Nishihama, Shogo Miyake, Nobuhiro Takahashi, and Yutaka Takaguchi* Graduate School of Environmental and Life Science, Okayama University 3-1-1 Tsushima-Naka, Kita-Ku, Okayama 700-8530 JAPAN Corresponding to Y. Takaguchi (E-mail: [email protected]) or T. Tajima (E-mail: [email protected]) Photoinduced polymerization of thiophene is considered to be useful for the
production of electronic devices materials in thin film forms. Various strategies have
been reported to polymerize thiophene derivatives photochemically.1 On the other hand,
photoinduced electron transfer systems of poly(thiophene) derivatives and C60 are of
interest in view of organic photovoltaic devices. From this point of view, photoinduced
polymerization of terthiophene-C60 interconnected system is of great interest. Although
Murata and Komatsu reported the preparation of terthiophene-C60 dyad thin films,
which was polymerized electrochemically on an electrode surface, and its
photoelectrochemical property2 much less is known about the photopolymerization of
terthiophene-C60 dyad. Here we report the synthesis and electrochemical polymerization
of a new conjugate system based on terthiophene and C60, i.e., (terthiophene)4-
poly(amidoamine)-C60 pentad 1. Photopolymerizations of 1 and its photoelectro-
chemical properties are also investigated. Interestingly, photopolymerized film of the
(terthiophene)4-poly(amidoamine)-C60 pentad (Figure 1b) was much conductive than
pentad monomer 1 (Figure 1a).
Figure 1. Photocurrent response of a film of monomer 1 and photopolymerized film of 1.
1. M. Sangermano, F. Sordo, A. Chiolerio, Y. Yagci, Polymer 2013, 54, 2077.
2. a) Y. Murata, M. Suzuki, K. Komatsu, Org. Biomol. Chem. 2003, 1, 2624. b) T. Yamazaki, Y.
Murata, K. Komatsu, K. Furukawa, M. Morita, N. Maruyama, T. Yamao, S. Fujita, Org. Lett.
2004, 6, 4865. c) A. Han, J. Bai, Y. Murata, K. Komatsu, Heteroatom Chem. 2011, 22, 72.
Mir Wais Hosseini
Université de Strasbourg, Institut Le Bel 4, rue Blaise Pascal, CS 90032, 67081 Strasbourg, France Phone: +33-0368851323, Fax: +33-0368851325 [email protected] Mir Wais Hosseini is Professor of chemistry at the University of Strasbourg and Senior Member of the Institut Universitaire de France, Chair of Molecular Tectonics and director of the Molecular Tectonics Laboratory. He obtained a Ph. D degree in 1983 from the Univesity Louis Pasteur, Strasbourg under the supervision of Professor Jean-Marie Lehn. After spending 10 years at the CNRS as Research Assistant and Associate in the group of Professor Lehn, he assumed a postdoctoral position at Berkeley in the group of Professor K. N. Raymond. In 1990 he was hired as a full Professor. He was invited Professor at University of Geneva, Institute of Materials and Chemical Research, Tsukuba, JSPS Invited Professor at The University of Tokyo, Invited Professor at The Academia Sinica, Taipei, Taiwan; JSPS Invited Professor at The University of Kyoto and invited Professor at The University Hokkaido. 1. PhD Prize, Young Researcher Prize, Coordination and Organic Divisions awards of the French Chemical Society, Prize of "Academie Rhenane", Gheorghe Spacu Medal of the Romanian Chemical Society, French-Italian bi-national Prize, German-French bi-national Grignard-Wittig Prize, Silver Medal of CNRS, Alexander von Humboldt Research Award, Izatt-Christensen award, Fellow of the Royal Society of Chemistry (FRSC), Member of The European Academy of Sciences, Arts and Humanities, Member of Academia Europaea; Selected Reviews and Papers 1. M. W. Hosseini, Acc. Chem. Res., 2005, 38, 313-323.
Perspectives in Molecular Tectonics
Mir Wais Hosseini University of Strasbourg 4, rue Blaise Pascal, CS 90032, 67081 Strasbourg, France [email protected] The design and construction of periodic architectures in the crystalline phase are attracting considerable interest over the last two decades. For both design and analysis of molecular crystals, we have developed a strategy called molecular tectonics which is based on the formation of molecular networks through the design of complementary tectons or molecular construction units. The generation of molecular networks and subsequently of crystals is achieved by self-assembly processes based on repetitive molecular recognition events. This approach, combining supramolecular synthesis and self-assembly processes in the solid state, is operational and versatile and allows the design and construct a variety of complex purely organic or hybrid architectures. The approach will be presented and illustrated by a variety of tectons and networks. 1. M. W. Hosseini, Acc. Chem. Res., 38, 313 (2005). 2. M. W. Hosseini, Chem. Commun., Focus Article, ,582 (2005). 3. M. W. Hosseini, CrystEngComm., 6, 318 (2004). Yutaka TAKAGUCHI
Graduate School of Environmental and Life Science, Okayama University 3-1-1 Tsushima-Naka, Kita-ku, Okayama 700-8530, Japan Phone & Fax: +81-86-251-8903 E-mail: [email protected] Professor Yutaka Takaguchi was born in Kobe, Japan, in 1968. He received his Ph.D. degrees in Chemistry from the University of Tsukuba in 1996 under the supervision of Prof. Naomichi Furukawa, where he worked on the syntheses and properties of organochalcogen compounds. He then was a RIKEN Special Postdoctoral Researcher in the group of Prof. Yasuo Wakatsuki, during which period he worked on the development of metathesis reactions using ruthenium complexes. He joined the Faculty of Textile Science and Technology at Shinshu University as an assistant professor in 1996, where he worked on the photochemistry of various compounds including dendrimers, fullerenes, and chalcogen atoms. In 2002, he was appointed as an associate professor at Okayama University. His research interests include (1) chemistry of nanocarbons (fullerenes and carbon nanotubes), (2) self-assembly and photoproperties of molecular semiconductors, and (3) fabrication and properties of organic-inorganic hybrids having a hierarchical architecture. Selected Papers 1. Template-Free Fabrication of Cylindrical Macropore Array in SnO2. Y. Ozawa, T. Tajima, M. Nishi, T. Ohkubo, Y. Takaguchi, RSC Advances 2013, 3, 22949-22952.
2. Photosensitized Hydrogen Evolution from Water Using a Single-Walled Carbon Nanotube/Fullerodendron/SiO2 Coaxial Nanohybrid. T. Tajima, W. Sakata, T. Wada,
A. Tsutsui, S. Nishimoto, M. Miyake, Y. Takaguchi. Avd. Mater. 2011, 23,
5750-5754.
Fabrication and Photosensitizing Properties of Coaxial Nanohybrids
Based on Single-Walled Carbon Nanotube
Yutaka Takaguchi* Graduate School of Environmental and Life Science, Okayama University 3-1-1 Tsushima-Naka, Kita-ku, Okayama 700-8530, Japan Phone & Fax: +81-86-251-8903; E-mail: [email protected] The construction of well-organized nano- and meso-structures via biomimetic processes is of interest from the point of view of organic-inorganic hybrid materials. In particular, hybrid materials based on nanocarbons have attracted many attentions because of the potential applications for photofunctional materials. In this paper, we will describe our approach to fabricate the co-axial nanowire structure having single-walled carbon nanotube (SWCNT) core and other hierarchical architectures.1-5 Furthermore, their photosensitizing property to produce hydrogen from water will be discussed. For example, SWCNT/fullerodendron/Pt(II) complex was prepared via stepwise self-organization processes and used for the photosensitizer of hydrogen evolution from water (Fig. 1). h
Dendron + Pt(II) complex layer Fig. 1 (a) Schematic illustration and a TEM image of the coaxial structure of SWCNT/fullerodendron/Pt(II) complex
and (b) energy diagram for hydrogen evolution from water (path A: an ordinary three component system and path B:
the interconnected system).
1. H. Suzuki, Y. Iizumi, M. Tange, S.-K. Joung, A. Furube, T. Wada, T. Tajima, Y. Takaguchi, T. Okazaki, Fullerenes, Nanotubes and Carbon Nanostructures 2014, 22, 44-56.
2. Y. Sasada, T. Tajima, T. Wada, T. Uchida, M. Nishi, T. Ohkubo, Y. Takaguchi, New J. Chem. 2013, 37, 4214-4219.
3. T. Tajima, A. Tsutsui, T. Fujii, J. Takada, Y. Takaguchi. Polym. J. 2012, 44, 620-624.
4. T. Tajima, W. Sakata, T. Wada, A. Tsutsui, S. Nishimoto, M. Miyake, Y. Takaguchi, Avd. Mater. 2011, 23, 5750-5754.
5. A. S. D. Sandanayaka, Y. Takaguchi, Y. Sako, M. Tamura, O. Ito, Adv. Sci. Lett. 2010, 3,
Eric Monflier
Université d'Artois, UCCS UMR 8181 Faculté des Sciences Jean Perrin, Rue Jean Souvraz, SP 18-62307 Lens Cédex, France Phone: (+33) 3 21 79 17 72 Eric Monflier graduated from the Ecole Nationale Supérieure de Chimie de Lille (ENSCL) in 1989 and received his Ph.D. degree from the University of Lille in 1992 under the supervision of Professor Francis Petit in the field of organometallic chemistry and homogeneous catalysis. In 1992, he became Associate Professor at the University of Artois where he set up an independent research group working on aqueous organometallic catalysis. He was promoted to Full Professor in 1996. His current research interests are mainly in the field of supramolecular catalysis and catalysis in multiphase systems. He has played a key role in the development of efficient supramolecular mass transfer promoters for aqueous organometallic catalysis. He is currently head of the research group "Catalysis and Supramolecular Chemistry" and has authored more than 180 international scientific publications, 21 book chapters, and 12 Eric Monflier received the « Prix de la Division Catalyse » from French Chemical Society in 1996, the « Prix des Techniques Innovantes pour l'Environnement » from French agency for environment and energy management in 2004, and the « Prix de l'Innovation et de la Valorisation de la Recherche » from OSEO - French innovation Transition metal catalysis in water assisted by cyclodextrins
Eric Monflier Université d'Artois, UCCS UMR 8181, Faculté des Sciences Jean Perrin, Rue Jean Souvraz, SP 18-62307 Lens Cédex, France. During the past decade, ecological requirements have pressed chemists to develop clean catalytic processes and technologies. In this context, the immobilization of homogeneous or heterogeneous transition metal catalysts in an aqueous phase appears as an eco-friendly technique to produce organic compounds. Indeed, the catalyst can be easily recovered in an active form at the end of reaction by decantation of the aqueous and organic phases and the production costs are significantly lower. However, the scope of aqueous catalysis is greatly reduced by the low solubility of most organic substrates in water and by the need to synthesize water-soluble ligands or stabilizing agents to immobilize the catalyst in water. In this lecture, we will demonstrate that cyclodextrins are very useful compounds to develop catalytic processes in water.1 These cyclic oligosaccharides can be used as mass transfer promoters, ligands platforms or dispersing and stabilizing agents of metallic nanoparticles or supported metals. The possibility to use the cyclodextrins in other green solvents will also be briefly discussed.2 1. Recent review: F. Hapiot, A. Ponchel, S. Tilloy, E. Monflier, C. R. Chimie, 2011, 14, 149; F. Hapiot, H. Bricout, S. Tilloy, E. Monflier, Eur. J. Inorg. Chem. 2012, 1571-1578; S. Noël, B. Léger, A. Ponchel, K. Philippot, A. Denicourt-Nowicki, A. Roucoux, E. Monflier, Catal. Today, 2014, 235, 20-32; F. Hapiot, H. Bricout, S. Menuel, S. Tilloy, E. Monflier, Catal. Sci. Technol., 2014, 4, 1899-1908. 2. C. Tortosa Estorach, M. Giménez-Pedrós, A.M. Masdeu-Bultó, A.D. Sayede, E. Monflier, Eur. J. Inorg. Chem. 2008, 2659; F. Wyrwalski, B. Léger, C. Lancelot, A. Roucoux, E. Monflier, A. Ponchel, Appl. Catal. A Gen. 2011, 391, 334-341; F. Jerome, M. Ferreira, H. Bricout, S. Menuel, E. Monflier, S. Tilloy, Green Chem.,

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