Intermolecular Alkene Difunctionalization via Gold-Catalyzed Oxyarylation

Angew Chem Int Ed Engl. 2020 Nov 9;59(46):20470-20474. doi: 10.1002/anie.202009636. Epub 2020 Sep 3.

Abstract

The gold-catalyzed intermolecular oxyarylation of alkenes is reported. This work employed the oxidative addition of aryl iodides to Me-DalphosAu+ for the formation of a AuIII -Ar intermediate. The better binding ability of alkenes over O nucleophiles ensured the success of intermolecular oxyarylation, giving desired products with a broad substrate scope and high efficiency (>50 examples with up to 95 % yield). One-pot converting of methoxy groups into other nucleophiles allowed achieving alkene difunctionalization with the construction of C-N, C-S, and C-C bonds under mild conditions.

Keywords: alkenes; gold redox catalysis; hemilabile (P,N) ligands; oxidative addition; oxyarylation.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Gold / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alkenes
  • Gold