Deacylative Thiolation by Redox-Neutral Aromatization-Driven C-C Fragmentation of Ketones.

ABSTRACT: Herein we report the development of deacylative thiolation of diverse methyl ketones. The reaction is redox-neutral, and heavy-metal-free, which provides a new way to introduce thioether groups site-specifically to unactivated aliphatic positions. It also features excellent functional group tolerance and broad substrate scope, thus allowing late-stage derivatization. The process benefits from efficient condensation between the activation reagent and ketone substrates, which triggers aromatization-driven C-C fragmentation and rapid radical coupling with thiosulfonates. Experimental and computational mechanistic studies suggest the involvement of a radical chain pathway.

SUBMITTER: Zhou X 

PROVIDER: S-EPMC10240504 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature