4.8 Article

Palladium Catalyzed Diaryl Sulfoxide Generation from Aryl Benzyl Sulfoxides and Aryl Chlorides

Journal

ORGANIC LETTERS
Volume 17, Issue 5, Pages 1168-1171

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00092

Keywords

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Funding

  1. National Science Foundation [CHE-1152488]
  2. Spanish MINECO [CTQ2012-38594-C02-01]
  3. Institute of Chemical Research of Catalonia (ICIQ) Foundation
  4. Vagelos Integrated Program in Energy Research
  5. Division Of Chemistry
  6. Direct For Mathematical & Physical Scien [1152488] Funding Source: National Science Foundation

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Diaryl sulfoxides are synthesized from aryl benzyl sulfoxides and aryl chlorides via three sequential catalytic cycles all promoted by a NiXantPhos-based palladium catalyst. The key step is S-arylation of a sulfenate anion. An air- and moisture-stable precatalyst derived from NiXantPhos efficiently facilitates the transformation. Various functional groups, including those with acidic protons, were tolerated. This method can also be extended to methyl and dibenzyl sulfoxides substrates.

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