Gold-Catalyzed Oxidation of Thioalkynes to Form Phenylthio Ketene Derivatives via a Noncarbene Route

Pankaj Sharma, Rahulkumar Rajmani Singh, Sovan Sundar Giri, Liang Yu Chen, Mu Jeng Cheng, Rai Shung Liu

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Gold-catalyzed oxidations of thioalkynes with 8-methylquinoline oxides afford 2-phenylthioketenes that can be trapped efficiently with alcohols. The synthetic utility is manifested by terminal and internal thioalkynes over a wide scope, bearing esters, ketones, alkyl, and oxime substituents. Our density functional theory calculations suggest that gold-catalyzed oxidations of terminal and internal thioalkynes with 8-methylquinoline oxides generate gold-bound ketene intermediates without the intermediacy of α-oxo gold carbene.

Original languageEnglish
Pages (from-to)5475-5479
Number of pages5
JournalOrganic Letters
Volume21
Issue number14
DOIs
Publication statusPublished - 2019 Jul 5

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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