Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines

Pui Kin Tony Lo, Gwyndaf A. Oliver and Michael C. Willis*

*Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, United Kingdom, Email: michael.willischem.ox.ac.uk

P. K. T. Lo, G. A. Oliver, M. C. Willis, J. Org. Chem., 2020, 85, 5753-5760.

DOI: 10.1021/acs.joc.0c00334

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Abstract

The addition of an organometallic reagent to the commercially available DABSO as sulfur dioxide surrogate generates a metal sulfinate which is reacted with thionyl chloride. Trapping of the formed sulfinyl chloride intermediates in situ with a variety of nitrogen nucleophiles provides sulfinamides in good yields. The overall reaction is performed at room temperature in only 1.5 h.

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A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides

M. Ding, Z.-X. Zhang, T. Q. Davies, M. C. Willis, Org. Lett., 2022, 24, 1711-1715.

DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide Preparation

H. Woolven, C. Gonzáles-Rodríguez, I. Marco, A. L. Thompson, M. C. Willis, Org. Lett., 2011, 13, 4876-4878.

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Key Words

aminosulfinylation, amination

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ID: J42-Y2020