Preparing glycosyl benzothiazoles from 2-isocyanoaryl thioethers and glycosyl radicals under thermal conditions

Abstract

Herein, we report a method for preparing glycosyl benzothiazoles via radical cascade cyclization, in which glycosyl radicals are generated from readily available and bench-stable allyl glycosyl sulfones. This cascade reaction proceeds under simple conditions and tolerates a broad substrate scope in high yield with excellent stereoselectivity. Mechanistic studies support that the reactions proceed via the intermediacy of imidoyl radicals, which attack the appended sulfide unit by a S_H2 process to forge the thiazole ring.