Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant

Jin Wang, Shuyao Zhang, Chang Xu, Lukasz Wojtas, Novruz G. Akhmedov, Hao Chen, Xiaodong Shi

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

Stereoselective thioallylation of alkynes under possible gold redox catalysis was accomplished with high efficiency (as low as 0.1 % catalyst loading, up to 99 % yield) and broad substrate scope (various alkynes, inter- and intramolecular fashion). The gold(I) catalyst acts as both a π-acid for alkyne activation and a redox catalyst for AuI/III coupling, whereas the sulfonium cation generated in situ functions as a mild oxidant. This novel methodology provides an exciting system for gold redox catalysis without the need for a strong oxidant.

Original languageEnglish (US)
Pages (from-to)6915-6920
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number23
DOIs
StatePublished - Jun 4 2018
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • alkynes
  • gold redox catalysis
  • sulfonium cations
  • thioallylation
  • vinyl gold intermediates

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