Palladium-Catalyzed Amination of Aryl Sulfoxides

• Yoshida, Yuto

  Department of Chemistry, Graduate School of Science, Kyoto University

• Otsuka, Shinya

  Department of Chemistry, Graduate School of Science, Kyoto University

• Nogi, Keisuke

  Department of Chemistry, Graduate School of Science, Kyoto University

• Yorimitsu, Hideki

  Department of Chemistry, Graduate School of Science, Kyoto University

Abstract

Amination of diaryl sulfoxides with anilines and alkylamines has been accomplished under palladium/N-heterocyclic carbene (NHC) catalysis. Owing to its electron deficiency, the leaving arenesulfenate anion would be smoothly released from the palladium center to result in uneventful catalyst turnover under milder reaction conditions in comparison with previous C–S bond amination reactions. This amination accommodated a wider range of functional groups such as silyl, boryl, methylsulfanyl, and halogen moieties. Regioselective amination of unsymmetrical diaryl sulfoxides was also executed by means of steric bias.

Journal

• Organic Letters

  Organic Letters 20 (4), 1134-1137, 2018-02-16

  American Chemical Society (ACS)

Keywords

• Organic Chemistry
• Physical and Theoretical Chemistry
• Biochemistry

Details

• CRID: 1050845760784917120
• NII Article ID: 120006406842
• ISSN: 15237060
• ISSN: 15237052
• DOI: 10.1021/acs.orglett.8b00060
• HANDLE: 2433/229509
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.8b00060
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN