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)

Research output: Contribution to journalArticleAcademicpeer-review

20 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 languageEnglish
Pages (from-to)720-725
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number2
Early online date27 Dec 2019
DOIs
Publication statusPublished - 15 Jan 2020

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