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Visible‐Light‐Enabled Direct Decarboxylative N‐Alkylation
Author(s) -
Nguyen Vu T.,
Nguyen Viet D.,
Haug Graham C.,
Vuong Ngan T. H.,
Dang Hang T.,
Arman Hadi D.,
Larionov Oleg V.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201916710
Subject(s) - alkylation , chemistry , decarboxylation , catalysis , acridine , primary (astronomy) , organic synthesis , organic chemistry , combinatorial chemistry , astronomy , physics
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.