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 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.