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Quentin GAIGNARD-GAILLARD a obtenu le prix du meilleur poster

Quentin GAIGNARD-GAILLARD, doctorant dans le groupe du Pr. Jean-Luc Renaud, a obtenu le prix du meilleur poster intitulé « Room-Temperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined Iron(II) Complex Using Hydrogen » lors du congrès IUPAC 2019 qui s’est déroulé à Paris du 7 au 12 Juillet dernier.

 

Voici le résumé de son poster :

 

Room Temperature Chemoselective Reductive Alkylation of Amines

Catalyzed by a Well-Defined Iron(II) Complex using Hydrogen.

 Quentin Gaignard Gaillard,a Alexis Lator,a Sylvain Gaillard,a Albert Poater,b Jean-Luc Renauda

a Normandie Univ., LCMT, ENSICAEN, UNICAEN, CNRS, 6 boulevard du Maréchal Juin,14000 Caen, France.

b Departament de Química, Institut de Química Computacional i Catàlisi (IQCC), University of Girona, c/Mª Aurèlia Capmany 69, 17003 Girona, Catalonia, Spain.

Email: quentin.gaignard-gaillard@ensicaen.fr

 

Economic constraints and environmental concerns in chemistry have led to increased demand for the replacement of noble metals used in chemical processes by Earth-abundant ones. Iron-catalyzed reduction has received intensive attention and some iron complexes have shown activities and selectivities that are competitive with those of noble metals.[1] However, exchanging noble metals for cheap, abundant, and biocompatible iron complexes to perform reduction is not the sole criterion to render such complexes attractive for industrial applications, the catalytic activities and the price of the ligand must also be taken into account.[2] In our ongoing research on iron-catalyzed reduction and alkylation,[3,4] a new cyclopentadienyl iron(II) tricarbonyl complex has been designed and applied in reductive alkylation.[5] This phosphine-free iron complex is the first Earth-abundant metal complex able to catalyze at room temperature the chemoselective reductive alkylation of various functionalized amines with functionalized aldehydes (alkenes, esters, ketones, acetals, unprotected hydroxyl group, phosphine, Scheme 1).[5]

Scheme 1. Iron(II)-catalyzed chemoselective reductive alkylation of amines.

 

References
[1] a) I. Bauer, H.-J. Knölker, Chem. Rev. 2015, 115, 3170. b) D. Wei, C. Darcel, Chem. Rev. 2019, 119, 2550. c) L. Alig, M. Fritz, S. Schneider, Chem. Rev. 2019, 119, 2681. d) D. S. Mérel, M.-L. Tran Do, S. Gaillard, P. Dupau, J.-L. Renaud, Coord. Chem. Rev. 2015, 288, 50.
[2] P. Dupau, M.-L. Tran Do, S. Gaillard, J.-L. Renaud, Angew. Chem. Int. Ed. 2014, 53, 13004.
[3] a) A. Lator, S. Gaillard, A. Poater, J.-L. Renaud, Chem. Eur. J. 2018, 24, 5770. b) T.-T. Thai, D. S. Mérel, A. Poater, S. Gaillard, J.-L. Renaud, Chem. Eur. J. 2015, 21, 7066. c) A. Pagnoux-Ozherelyeva, N. Pannetier, M. D. Mbaye, S. Gaillard, J.-L. Renaud, Angew. Chem. Int. Ed. 2012, 51, 4976.
[4] a) L. Bettoni, C. Seck, M. D. Mbaye, S. Gaillard, J.-L. Renaud, Org. Lett. 2019, 21, 3057. b) A. Lator, S. Gaillard, A. Poater, J.-L. Renaud, Org. Lett. 2018, 20, 5985. c) C. Seck, M. D. Mbaye, S. Gaillard, J.-L. Renaud, Adv. Synth. Catal 2018, 360, 4640. d) C. Seck, M. D. Mbaye, S. Coufourier, A. Lator, J.-F. Lohier, A. Poater, T. R. Ward, S. Gaillard, J.-L. Renaud, ChemCatChem. 2017, 9, 4410.
[5] b) A. Lator, Q. Gaignard Gaillard, D. S. Mérel, J.-F. Lohier, S. Gaillard, A. Poater, J.-L. Renaud, J. Org. Chem. 2019, 84, in press.

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