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Visible‐Light‐Driven, Copper‐Catalyzed Decarboxylative C(sp 3 )−H Alkylation of Glycine and Peptides
Author(s) -
Wang Chao,
Guo Mengzhun,
Qi Rupeng,
Shang Qinyu,
Liu Qiang,
Wang Shan,
Zhao Long,
Wang Rui,
Xu Zhaoqing
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201809400
Subject(s) - alkylation , glycine , chemistry , catalysis , amino acid , photocatalysis , copper , combinatorial chemistry , visible spectrum , photochemistry , organic chemistry , stereochemistry , biochemistry , materials science , optoelectronics
Abstract Despite a well‐developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible‐light‐induced Cu‐catalyzed decarboxylative C(sp 3 )−H alkylation of glycine for preparing α‐alkylated unnatural α‐amino acids. It merits mentioning that the mild conditions and the good functional‐group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical–radical coupling pathway is involved in the reaction.