Sindija Lapcinska, Pavels Dimitrijevs, P. Arsenyan
Oct 30, 2022
Citations
0
Influential Citations
3
Citations
Journal
The Journal of organic chemistry
Abstract
A mild and efficient method for preparation of 3-sulfenyl and 3-selenyl coumarins and quinolinones mediated by artificial light or sunlight is presented. The elaborated protocol highlights the use of nonyl acridine orange as a photocatalyst to generate a sulfenyl radical from thiols that is further trapped by a heterocycle. The utility of the protocol is justified by a diverse scope of thiols, including short cysteine-containing peptides. The same reaction conditions can be applied for preparation of 3-selenyl coumarins and quinolinones. Various protected and unprotected selenocysteine-containing peptides were successfully utilized demonstrating high tolerance for amino acids with sensitive groups (Arg, Lys, Trp, His, and Tyr).