Palladium(II)-catalyzed aerobic hydroalkoxylation of styrenes containing a phenol

J Am Chem Soc. 2006 Mar 8;128(9):2794-5. doi: 10.1021/ja0585533.

Abstract

An intermolecular Pd-catalyzed hydroalkoxylation of styrenes that contain a phenol is presented. The reaction can be performed on terminal, disubstituted, and trisubstituted olefins in a variety of alcoholic solvents. Initial mechanistic data suggest a mechanism that involves oxidation of the alcoholic solvent to provide a Pd-hydride that inserts into an olefin. This is followed by formation of a quinone methide and subsequent addition of an alcohol to yield the hydroalkoxylated product.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Ethers / chemical synthesis*
  • Hydroxylation
  • Indolequinones / chemistry
  • Ketones / chemical synthesis*
  • Oxidation-Reduction
  • Palladium / chemistry
  • Phenols / chemical synthesis*
  • Phenols / chemistry*
  • Styrenes / chemistry*

Substances

  • Alkenes
  • Ethers
  • Indolequinones
  • Ketones
  • Phenols
  • Styrenes
  • quinone methide
  • Palladium