Synthesis of α-Aryl Primary Amides from α-Silyl Nitriles and Aryl Sulfoxides through [3,3]-Sigmatropic Rearrangement

Fan Luo, Hui Zhou, Xiao Bei Chen, Xue Jun Liu, Xiao Dong Chen, Peng Fei Qian, Xin Ping Wu, Wei Wang, Shi Lei Zhang

Research output: Contribution to journalArticlepeer-review

Abstract

A simple and efficient protocol was developed for the preparation of challenging α-aryl primary amides. This metal-free coupling process was triggered by TfOH-promoted electrophilic activation of α-silyl nitrile to generate keteniminium ion species, followed by reaction with aryl sulfoxide through [3,3]-sigmatrophic rearrangement to provide the target product. To the best of our knowledge, α-silyl nitrile has been rarely used as a pro-electrophilic reagent. Computational investigations confirmed the transient existence of a highly electrophilic keteniminium intermediate.

Original languageEnglish (US)
Pages (from-to)1700-1705
Number of pages6
JournalOrganic Letters
Volume24
Issue number8
DOIs
StatePublished - Mar 4 2022
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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