Visible-Light-Enabled Direct Decarboxylative N-Alkylation.
The development of efficient and selective C-N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction.
['Nguyen|Vu T|VT|', 'Nguyen|Viet D|VD|', 'Haug|Graham C|GC|', 'Vuong|Ngan T H|NTH|', 'Dang|Hang T|HT|', 'Arman|Hadi D|HD|', 'Larionov|Oleg V|OV|0000-0002-3026-1135']
D000166:Acridines D000478:Alkylation D000588:Amines D000814:Aniline Compounds D002384:Catalysis D006571:Heterocyclic Compounds D010084:Oxidation-Reduction
amination carboxylic acids copper catalysis photocatalysis visible light