Harnessing Sulfinyl Nitrenes: A Unified One-Pot Synthesis of Sulfoximines and Sulfonimidamides

Thomas Q. Davies, Michael J. Tilby, Jack Ren, Nicholas A. Parker, David Skolc, Adrian Hall, Fernanda Duarte and Michael C. Willis*

*Department of Chemistry, Chemistry Research Laboratories, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K., Email: michael.willischem.ox.ac.uk

T. Q. Davis, M. J. Tilby, J. Ren, N. A. Parker, D. Skolc, A. Hall, F. Duarte, M. C. Willis, J. Am. Chem. Soc., 2020, 142, 15445-15453.

DOI: 10.1021/jacs.0c06986

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Abstract

A one-pot approach to both sulfoximines and sulfonimidamides exploits the high electrophilicity of sulfinyl nitrenes. These rare reactive intermediates are generated from a sulfinylhydroxylamine (R-O-N=S=O) reagent through an N-O bond fragmentation process. Addition of carbon and nitrogen nucleophiles enables the synthesis of sulfoximines and sulfonimidamides in just 15 min.

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Nickel(II)-Catalyzed Addition of Aryl and Heteroaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides, and Primary Sulfonamides

P. K. T. Lo, M. C. Willis, J. Am. Chem. Soc., 2021, 143, 15576-15581.

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Key Words

Sulfoximines, Sulfonimidamides

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ID: J48-Y2020