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

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

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)
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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.
Original languageEnglish
JournalAsian Journal of Organic Chemistry
VolumeEarly View
Early online date18 Nov 2019
DOIs
Publication statusE-pub ahead of print - 18 Nov 2019

Keywords

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

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