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Direct N‐Acylation of Sulfoximines with Aldehydes by N‐Heterocyclic Carbene Catalysis under Oxidative Conditions

Direct N‐Acylation of Sulfoximines with Aldehydes by N‐Heterocyclic Carbene Catalysis under... An active acyl donor intermediate generated in situ from an aldehyde by oxidative N‐heterocyclic carbene (NHC)‐catalysis enables direct acylation of NH‐sulfoximine, affording various N‐acylsulfoximines in excellent yields. The reaction was performed with an inexpensive carbene catalyst and easily accessible bisquinone oxidant. This straightforward transformation demonstrated a broad substrate scope with respect to sulfoximines and aldehydes. Importantly, the method allowed amidation of several unactivated aliphatic aldehydes in good‐to‐moderate yields. Preparative synthesis of N‐acylsulfoximine (up to >2 g) was achieved with this simple method. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Direct N‐Acylation of Sulfoximines with Aldehydes by N‐Heterocyclic Carbene Catalysis under Oxidative Conditions

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References (64)

Publisher
Wiley
Copyright
© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201600163
Publisher site
See Article on Publisher Site

Abstract

An active acyl donor intermediate generated in situ from an aldehyde by oxidative N‐heterocyclic carbene (NHC)‐catalysis enables direct acylation of NH‐sulfoximine, affording various N‐acylsulfoximines in excellent yields. The reaction was performed with an inexpensive carbene catalyst and easily accessible bisquinone oxidant. This straightforward transformation demonstrated a broad substrate scope with respect to sulfoximines and aldehydes. Importantly, the method allowed amidation of several unactivated aliphatic aldehydes in good‐to‐moderate yields. Preparative synthesis of N‐acylsulfoximine (up to >2 g) was achieved with this simple method.

Journal

Asian Journal of Organic ChemistryWiley

Published: Jul 1, 2016

Keywords: ; ; ; ;

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