4.7 Article

Direct C(sp2)-H Arylsulfonylation of Enamides via Iridium(III)-Catalyzed Insertion of Sulfur Dioxide with Aryldiazonium Tetrafluoroborates

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 15, Pages 3593-3598

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900257

Keywords

Organic catalysis; C-H functionalization; Insertion of sulfur dioxide; Enamides; beta-Amido sulfones

Funding

  1. Nanjing Tech University [39837137, 39837101, 3827401739]
  2. National Natural Science Foundation of China [21372210, 21672198, 21801129]
  3. State Key Program of National Natural Science Foundation of China [21432009]
  4. Natural science research projects in Jiangsu higher education institutions [18KJB150018]

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An iridium(III)-catalyzed three-component reaction of enamides, aryldiazonium tetrafluoroborates, and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) for the direct C(sp(2))-H arylsulfonylation of enamides is developed. This transformation provides a robust and straightforward approach for preparing a diverse array of beta-amidovinyl sulfones in moderate to excellent yields and high stereoselectivities without Light-emitting diode (LED) radiation. This transformation also features mild conditions, broad substrate scopes, and excellent functional group tolerance.

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