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Visible‐Light‐Promoted C(sp 3 )−H Alkylation by Intermolecular Charge Transfer: Preparation of Unnatural α‐Amino Acids and Late‐Stage Modification of Peptides
Author(s) -
Wang Chao,
Qi Rupeng,
Xue Hongxiang,
Shen Yuxuan,
Chang Min,
Chen Yaqiong,
Wang Rui,
Xu Zhaoqing
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914555
Subject(s) - chemistry , alkylation , electrophile , glycine , intermolecular force , amino acid , visible spectrum , salt (chemistry) , acceptor , combinatorial chemistry , leaving group , stereochemistry , photochemistry , organic chemistry , molecule , catalysis , biochemistry , physics , optoelectronics , condensed matter physics
Disclosed herein is the visible‐light‐promoted deaminative C(sp 3 )−H alkylation of glycine and peptides using Katritzky salts as electrophiles. Simple reaction conditions and excellent functional‐group tolerance provide a general strategy for the efficient preparation of unnatural α‐amino acids and precise modification of peptides with unnatural α‐amino‐acid residues. Mechanistic studies suggest that visible‐light‐promoted intermolecular charge transfer within a glycine–Katritzky salt electron donor‐acceptor (EDA) complex induces a single‐electron transfer process without the assistance of photocatalyst.