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Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes

Sandrine M. Hell, Claudio F. Meyer, Gabriele Laudadio, Antonio Misale, Michael C. Willis, Timothy Noël, Andrés A. Trabanco and Véronique Gouverneur*

*University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, United Kingdom, Email: veronique.gouverneurchem.ox.ac.uk

S. M. Hell, C. F. Meyer, G. Laudadio, A. Misale, M. C. Willis, T. Noël, A. A. Trabanco, V. Gouverneur, J. Am. Chem. Soc., 2020, 142, 720-725.

DOI: 10.1021/jacs.9b13071 (free Supporting Information)



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Abstract

Sulfamoyl chlorides can be easily activated by Cl-atom abstraction in the presence of a silyl radical. This mode of activation can be used for a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y.

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Key Words

sulfamoylation, TTMSS, photochemistry


ID: J48-Y2020