Visible‐Light‐Promoted C(sp3)−H Alkylation by Intermolecular Charge Transfer: Preparation of Unnatural α‐Amino Acids and Late‐Stage Modification of Peptides

Disclosed herein is the visible‐light‐promoted deaminative C(sp3)−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 p...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-05, Vol.59 (19), p.7461-7466
Main Authors: Wang, Chao, Qi, Rupeng, Xue, Hongxiang, Shen, Yuxuan, Chang, Min, Chen, Yaqiong, Wang, Rui, Xu, Zhaoqing
Format: Article
Language:English
Subjects:
Alkylation
Amino acids
Charge preparation
Charge transfer
Coordination compounds
cross-coupling
donor-acceptor complexes
Electron transfer
Glycine
Peptides
photochemistry
Salts
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Disclosed herein is the visible‐light‐promoted deaminative C(sp3)−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. Unnatural: The visible‐light‐promoted deaminative C(sp3)−H alkylation of glycine and peptides proceeds by 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201914555