Mechanochemical Decarboxylative Radical Couplings toward Nonanomeric S- and C- Glycosides

Herein, we disclose a mechanochemical decarboxylative functionalization for the assembly of nonanomeric S- and C-glycosides via a one-pot, two-step protocol. Using Hantzsch ester together with zinc powder as the combined reducing system, glycosyl radicals are generated and subsequently intercepted by a broad array of radical acceptors under catalyst-free and light-free conditions. This mechanochemical protocol tolerates a broad substrate scope and affords excellent stereoselectivity.