Non-Diazo C-H Insertion Approach to Cyclobutanones through Oxidative Gold Catalysis

Angew Chem Int Ed Engl. 2020 Sep 28;59(40):17398-17402. doi: 10.1002/anie.202003698. Epub 2020 Aug 11.

Abstract

Cyclobutanones are synthetically versatile compounds that often require extensive effort to access. Herein, we report a facile synthesis of cyclobutanones based on the C(sp3 )-H insertion chemistry of oxidatively generated gold carbenes. Various cyclobutanones were obtained in synthetically useful yields from substrates with minimal structural prefunctionalization. This discovery reveals new synthetic utilities of gold-catalyzed oxidative transformations of alkynones.

Keywords: C−H insertion; catalysis; cyclobutanone; gold carbene; oxidation.

Publication types

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

MeSH terms

  • Carbon / chemistry
  • Catalysis
  • Cyclobutanes / chemistry*
  • Gold / chemistry*
  • Hydrogen / chemistry
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Molecular Conformation
  • Oxidation-Reduction
  • Quantum Theory

Substances

  • Cyclobutanes
  • Ketones
  • carbene
  • Carbon
  • Gold
  • Hydrogen
  • Methane