N-Heterocyclic-Carbene-Catalyzed Sulfa-Michael additions

An efficient N‐heterocyclic carbene (NHC)‐catalyzed sulfa‐Michael addition of thiols and Michael acceptors was developed. In the presence of 5 mol % of the NHC catalyst, various thiols undergo conjugate addition with α,β‐unsaturated ketones, esters, amides, sulfones, or nitriles to afford β‐keto sul...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2015-04, Vol.4 (4), p.327-332
Main Authors: Li, Yuan-Zhen, Wang, Ying, Du, Guang-Fen, Zhang, Hai-Yan, Yang, Hong-Li, He, Lin
Format: Article
Language:English
Subjects:
enones
N-heterocyclic carbenes
Organic chemistry
sulfa-Michael addition
thiols
β-keto sulfides
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Summary:An efficient N‐heterocyclic carbene (NHC)‐catalyzed sulfa‐Michael addition of thiols and Michael acceptors was developed. In the presence of 5 mol % of the NHC catalyst, various thiols undergo conjugate addition with α,β‐unsaturated ketones, esters, amides, sulfones, or nitriles to afford β‐keto sulfides in good to excellent yields. Sulfa‐sufficiency: N‐heterocyclic carbenes act as strong Brønsted bases to catalyze sulfa‐Michael additions of thiols with different Michael acceptors to produce β‐keto sulfides in good to excellent yields. EWG=electron‐withdrawing group.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201402241