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Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

Research output: Contribution to journalArticle

DOI

Open Access Status

  • Embargoed (until 18/11/20)

Author(s)

Matthew West, Brodie Thomson, Julien C. Vantourout, Allan J. B. Watson

School/Research organisations

Abstract

We report the discovery, scope, and limitations of a Cu‐mediated sulfonamide N‐dealkylation/N‐arylation reaction. Specific secondary N‐alkyl sulfonamides undergo Cu‐mediated oxidative dealkylation followed by N‐arylation under Chan–Lam conditions. The reaction is relatively general, allowing the synthesis of a range of N‐aryl secondary sulfonamides in good yield. Mechanistic investigations determined the sequence of reaction events as well as the efficiency‐limiting events. Limitations in the methodology are also presented.
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Original languageEnglish
JournalAsian Journal of Organic Chemistry
VolumeEarly View
Early online date18 Nov 2019
DOIs
Publication statusE-pub ahead of print - 18 Nov 2019

    Research areas

  • Arylation, Boron, Copper, Cross-coupling, Oxidation

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