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

TitleEnvironmentally benign synthesis of beta-hydroxy sulfides using cyclic carbonates catalyzed by large-pore zeolites
Publication TypeJournal Article
Year of Publication2012
AuthorsUpare, PP, Kinage, AK, Shingote, SK, Gupte, SP
JournalGreen Chemistry Letters and Reviews
Volume5
Issue1
Pagination19-26
Date PublishedAUG
ISSN1751-8253
Keywordsbeta-hydroxy sulfide, ethylene carbonate, propylene carbonate, thiophenol, zeolite
Abstract

An efficient one-pot synthesis of beta-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 beta-hydroxy sulfides without the use of any solvent.

DOI10.1080/17518253.2011.574295
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)1.392
Divison category: 
Catalysis and Inorganic Chemistry
Chemical Engineering & Process Development