Silyl radical-mediated activation of sulfamoyl chlorides enables direct access to aliphatic sulfonamides from alkenes

Sandrine Hell; Claudio Meyer; Gabriele Laudadio; Antonio Misale; Michael Willis; Timothy Noël; Andres Trabanco; Veronique Gouverneur

doi:10.1021/jacs.9b13071

Silyl radical-mediated activation of sulfamoyl chlorides enables direct access to aliphatic sulfonamides from alkenes

Sandrine Hell, Claudio Meyer, Gabriele Laudadio, Antonio Misale, Michael Willis, Timothy Noël, Andres Trabanco, Veronique Gouverneur (Corresponding author)

Micro Flow Chemistry and Synthetic Methodology

Research output: Contribution to journal › Article › Academic › peer-review

88 Citations (Scopus)

Abstract

Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.

Original language	English
Pages (from-to)	720-725
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	2
Early online date	27 Dec 2019
DOIs	https://doi.org/10.1021/jacs.9b13071
Publication status	Published - 15 Jan 2020

Funding

We gratefully acknowledge Dr. Maurice Médebielle for insightful comments on the manuscript and Dr. Natan Straathof and Tim Mollner for discussions. This project has received funding from the European Union’s Horizon 2020 research and innovation program under the Marie Skłodowska-Curie grant agreement no. 721902. T.N. and G.L. acknowledge financial support from the Dutch Science Foundation (NWO) (VIDI, SensPhotoFlow, no. 14150).

Funders	Funder number
European Union's Horizon 2020 - Research and Innovation Framework Programme
Horizon 2020 Framework Programme
Marie Skłodowska‐Curie	721902
Nederlandse Organisatie voor Wetenschappelijk Onderzoek	14150

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abstract = "Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.",

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AU - Misale, Antonio

AU - Willis, Michael

AU - Noël, Timothy

AU - Trabanco, Andres

AU - Gouverneur, Veronique

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AB - Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.

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Silyl radical-mediated activation of sulfamoyl chlorides enables direct access to aliphatic sulfonamides from alkenes

Abstract

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