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Polystyrene‐Supported 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene as an Efficient and Reusable Catalyst for the Thiolysis of 1,2‐Epoxides under Solvent‐Free Conditions
Author(s) -
Fringuelli Francesco,
Pizzo Ferdinando,
Vittoriani Carla,
Vaccaro Luigi
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500791
Subject(s) - thiolysis , chemistry , ene reaction , catalysis , regioselectivity , polystyrene , alkyl , organic chemistry , aryl , organocatalysis , solvent , green chemistry , selectivity , combinatorial chemistry , reaction mechanism , enantioselective synthesis , polymer , polyphenol , proanthocyanidin , antioxidant
Polystyrene‐supported 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (PS‐TBD) is an effective basic catalyst for the thiolysis of the 1,2‐epoxides 1a – e by the aryl‐ and alkyl‐substituted thiols 2A – E under solvent‐free conditions while its activity is remarkably reduced in MeCN. The reactions are totally anti ‐diastereoselective and generally highly C‐β regioselective. The corresponding hydroxy sulfides have been isolated in excellent yields and the catalyst has been easily recovered and reused with no loss in terms of efficiency and selectivity of the process. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)