Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol

• DOI: 10.1021/acs.joc.9b01670
• Publication Date: 2019-08-08T13:57:22Z
• Authors: Xiantao Ma; Jing Yu; Ran Yan; Mengli Yan; Qing Xu
• Keywords: Thioether; Sodium thiosulfate

It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, specific synthesis of unsymmetrical thioethers via one-step formation two C-S bonds under catalyst-, additive-, solvent-free conditions. Mechanistic studies suggest that Na2S2O3·5H2O crucial generating key thiol intermediates byproduct NaHSO4, which then catalyzes dehydrative substitution alcohols thiols to afford thioethers.