Room-Temperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined Iron(II) Complex Using Hydrogen

Alexis Lator, Quentin Gaignard Gaillard, Delphine S. Mérel, Jean-François Lohier, Sylvain Gaillard, Albert Poater*, Jean-Luc Renaud*

*University of Girona, c/Maria Aurèlia Capmany 69, 17003 Girona, Catalonia, Spain; UNICAEN, CNRS, 6 boulevard du Maréchal Juin, 14000 Caen, France, Email: albert.poaterudg.edu, jean-luc.renaudensicaen.fr

A. Lator, Q. G. Gaillard, D. S. Mérel, J.-F. Lohier, S. Gaillard, A. Poater, J.-L. Renau, J. Org. Chem., 2019, 84, 6813-6829.

DOI: 10.1021/acs.joc.9b00581

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Abstract

A cyclopentadienyl iron(II) tricarbonyl complex is able to catalyze a chemoselective reductive alkylation of various functionalized amines with functionalized aldehydes at room temperature. The reaction tolerates alkenes, esters, ketones, acetals, unprotected hydroxyl groups, and phosphines.

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Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol

A. Lator, S. Gaillard, A. Poater, J.-L. Renau, Org. Lett., 2018, 20, 5985-5990.

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Key Words

reductive amination, hydrogen

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ID: J42-Y2019