Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars

Org Lett. 2019 Jul 5;21(13):5132-5137. doi: 10.1021/acs.orglett.9b01730. Epub 2019 Jun 18.

Abstract

A general protocol for functionalization of glycosyl thiols has been reported. This protocol is based on a single-electron Ni/photoredox dual-catalyzed cross coupling between 1-thiosugars and a broad range of aryl bromides and iodides as well as alkenyl and alkynyl halides. This base-free method gives access to a series of functionalized thioglycosides in moderate to excellent yields with a perfect control of the anomeric configuration. Moreover, it has been shown that this methodology may be transposed successfully to the continuous-flow photoredox chemistry.

Publication types

  • Research Support, Non-U.S. Gov't