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8274697 
Journal Article 
Promoting effect of crystal water leading to catalyst-free synthesis of heteroaryl thioether from heteroaryl chloride, sodium thiosulfate pentahydrate, and alcohol 
Ma, X; Yu, J; Yan, R; Yan, M; Xu, Q 
2019 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
American Chemical Society 
84 
17 
11294-11300 
English 
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. © 2019 American Chemical Society.