Environmentally benign synthesis of β-hydroxy sulfides using cyclic carbonates catalyzed by large-pore zeolites

Green Chemistry Letters and Reviews

Pravin P. Upare¹ 

关键词: zeolite;    β-hydroxy sulfide;    ethylene carbonate;    propylene carbonate;    thiophenol;   

DOI  :  10.1080/17518253.2011.574295

学科分类：化学（综合）

来源: Taylor & Francis

【 摘 要 】

An efficient one-pot synthesis of β-hydroxy sulfides from thiophenol and cyclic carbonates catalyzed by large-pore zeolites has been reported. Reaction of thiophenol with ethylene carbonate in the presence of the Na-X zeolite catalyst gave the highest yield of 2-(phenylthio)ethanol (100%), while reaction with propylene carbonate a highest yield of regioselective product 1-(phenylthio)propan-2-ol was obtained (97%). Enantiomerically pure 1,2-propylene carbonate gave highly regioselective and stereospecific phenylthiopropanol, demonstrating that original chirality of propylene carbonate is retained. A plausible mechanism has been proposed for zeolite-catalyzed transformation involving a chemoselective nucleophilic attack of thiophenoloxide ion onto the less-substituted carbon of cyclic carbonate. The Na-X zeolite catalyst is recyclable and provides advantages of green chemistry approach to the synthesis of β-hydroxy sulfides without the use of any solvent.

【 授权许可】

Unknown