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

Xiantao Ma, Jing Yu, Ran Yan, Mengli Yan, Qing Xu

J Org Chem. 2019 Sep 6;84(17):11294-11300.

PMID: 31393123

Abstract:

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, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP10102177-B Sodium thiosulfate pentahydrate Sodium thiosulfate pentahydrate 10102-17-7 Price
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