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Copper-Catalyzed, Aerobic Synthesis of NH-Sulfonimidamides from Primary Sulfinamides and Secondary Amines

Peng Wu, Joachim Demaerel, Deshen Kong, Ding Ma and Carsten Bolm*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Email: carsten.bolmoc.rwth-aachen.de

P. Wu, J. Demaerel, D. Kong, D. Ma, C. Bolm, Org. Lett., 2022, 24, 6988-6992.

DOI: 10.1021/acs.orglett.2c02804


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Abstract

NH-Sulfonimidamides are prepared in good yields by a ligand-free copper-catalyzed coupling of primary sulfinamides with secondary amines in the presence of air as the terminal oxidant. The reaction occurs at room temperature and shows good functional group tolerance. A sulfanenitrile is proposed as an intermediate in this oxidative amination.

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proposed mechanism



General procedure for the synthesis of sulfonimidamides from sulfinamides

A mixture of sulfinamide (0.1 mmol), alkylamine (0.2 mmol, 2 equiv), CuBr2 (20 mol %), and toluene (1 mL) in a 10 mL sealed vial was stirred for 12 h at room temperature, and then concentrated in vacuo. The sulfonimidamide was purified by flash column chromatography using n-pentane/ethyl acetate as the eluent.


Key Words

sulfonimidamides, oxygen


ID: J54-Y2022