4.5 Article

N-Heterocyclic-Carbene-Catalyzed Sulfa-Michael additions

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 4, Issue 4, Pages 327-332

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201402241

Keywords

beta-keto sulfides; enones; N-heterocyclic carbenes; sulfa-Michael addition; thiols

Funding

  1. National Natural Science Foundation of China [21262027]
  2. Natural Science Foundation of Shihezi University [2011ZRKETD-04, 2012ZRKXJQ06, 2012ZRKXYQYD01]
  3. Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan [KF201301]

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An efficient N-heterocyclic carbene (NHC)-catalyzed sulfa-Michael addition of thiols and Michael acceptors was developed. In the presence of 5mol% of the NHC catalyst, various thiols undergo conjugate addition with alpha,beta-unsaturated ketones, esters, amides, sulfones, or nitriles to afford beta-keto sulfides in good to excellent yields.

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