Rh(III)-catalyzed and alcohol-involved carbenoid C-H insertion into N-phenoxyacetamides using α-diazomalonates

Chem Commun (Camb). 2015 Apr 7;51(27):5868-71. doi: 10.1039/c5cc00354g. Epub 2015 Mar 2.

Abstract

Here we report a new and mild Rh(III)-catalyzed and alcohol-involved carbenoid C-H insertion into N-phenoxyacetamides using α-diazomalonates. This reaction provided a straightforward way for installing both an α-quaternary carbon center and a free-OH moiety into the phenyl ring, thus giving access to useful 2-(2-hydroxyphenyl)-2-alkoxymalonates with good substrate/functional group tolerance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Malonates / chemistry*
  • Methanol / chemistry
  • Molecular Structure
  • Phenoxyacetates / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Azo Compounds
  • Malonates
  • Phenoxyacetates
  • Carbon
  • Rhodium
  • Methanol