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N-heterocyclic carbene–catalyzed sulfa-Michael addition of enals

Abstract

An efficient N-heterocyclic carbene (NHC) catalyzed sulfa-Michael addition (SMA) between enals and thiols has been developed. Under the catalysis of 10 mol% stable free carbene IPr and with 20 mol% hexafluoroisopropanol (HFIP) as additive, enals react with a variety of thiols to afford the SMA adducts in 54-98% yields. In this process, the free carbene preferentially interacts with thiols through hydrogen-bonding and no NHC-catalyzed extended Umpolung transformations were observed.

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Publication details

The article was received on 18 Sep 2017, accepted on 13 Nov 2017 and first published on 13 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC07269D
Citation: Chem. Commun., 2017, Accepted Manuscript
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    N-heterocyclic carbene–catalyzed sulfa-Michael addition of enals

    Z. Cong, Y. Li, G. Du, C. Gu, B. Dai and L. He, Chem. Commun., 2017, Accepted Manuscript , DOI: 10.1039/C7CC07269D

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