Marc Taillefer 09mai2023

CAPT Seminar - Pr. Marc TAILLEFERMardi, 15h00 - Amphi IPREM

Le 9 mai 2023 à 14h00

Pr. Marc Taillefer
(University of Montpellier, France / CNRS, ICGM, ENSCM)

"Transition-Metal Catalyzed or Transition Metal Free C-C and C-Heteroatom Bond Formation
From the discovery to mechanisms and industrial applications"

Abstract:
N-, O-, C-, -P or S-arylation of nucleophiles from aromatic halides occurs with high yields using transition metal free, Cu, Mn or Fe based catalytic systems.¹ Mildness, low cost and simplicity are features of our methods, which make them particularly well suited for industrial scale syntheses where financial and environmental issues are of greater concern. A lot of companies adopted our technologies, especially using copper catalysts, which will assert its position in the industry over the next decades. An example will be presented and investigations concerning the mechanisms will be particularly detailed.
The hydrofunctionalisation of unsaturated alkyl chains, catalysed by Cu, Fe or light irradiation, as well as a new method allowing the functionalization of biosourced alcohols via their activation under transition metal-free conditions, will also be presented.²

References
¹ a) Taillefer M, Cellier PP, Cristau H-J, Spindler JF, 2001 Fr 16547 (WO 03053885); b) Xia, N, Taillefer M, Angew. Chem. Int. Ed. 2009, 48, 337. c) Pichette Drapeau M, Fabres I, Ciofini I, Grimaud L, Ollevier T, Taillefer M, Angew. Chem. Int. Ed. 2015, 54, 10587; d) Hyde S, Veliks J, Liegault B, Grassi D, Tomlin P, Taillefer M, Le Gouverneur V, Angew. Chem. Int. Ed. 2016, 55, 3785; e) Perego LA, Blieck R, Groué A, Monnier F, Taillefer M, Ciofini I, Grimaud L, ACS Catal. 2017, 7 (7), 4253; f) Liu Y, Bergès J, Zaïd Y, Ouazzani F, Van Der Lee A, Harakat D, Clot E, Jaroschik F, Taillefer M, Journal of Organic Chemistry 2019, 84, 4413; g) Zaid Y, Mboyi CD, Pichette Drapeau M, Radal L, Ouazzani F, Rodi YK, Ollevier T, Taillefer M, Organic Letters 2019, 21, 1564; h) Abdine R, Kurpik G, Walczak A, Aeash SAA, Stefankiewicz AR, Monnier F, Taillefer M, Journal of Catalysis, 376, 2019, 119. i) Bergès J, Zaïd Y, Tlili A, Sotiropoulos J-M, Taillefer M, EurJOC, 2021 (10), 1559.

² a) X Liu, JM Sotiropoulos, M Taillefer, Eur. J. Org. Chem. 2022, e202200631; b) L Geniller, M Taillefer, F Jaroschik, A Prieto, Chem. Eur. J., 2022, 28, e202201495; c) X Liu, JM Sotiropoulos, M Taillefer, Organic Chemistry Frontiers, 2021, 8, 5112; d) L Pages, S Lemouzy, M Taillefer, F Monnier, Journal of Organic Chemistry, 2021, 86, 21,15695; e) R Blieck, S Lemouzy, A van der Lee, M Taillefer, F Monnier, Organic Letters, 2021, 23 (23), 9199; f) L. Geniller, M. Taillefer, F. Jaroschik, A. Prieto, Adv. Synth.Catal. 2022, 364, 4249; g) A Prieto, M Taillefer, Organic Letters, 2021, 23 (4), 1484; h) L. Pagès, M. Bouquin, F. Jaroschik, F. Monnier, M. Taillefer, Journal of Organic Chemistry, 2023, 88, 21,15695,2, 1168.