Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization

Org Lett. 2011 Dec 2;13(23):6320-3. doi: 10.1021/ol202881q. Epub 2011 Nov 9.

Abstract

An intramolecular cyclization cascade reaction has been developed utilizing a high valent palladium intermediate that generates a carbon-carbon and carbon-oxygen bond in a single transformation. This method provides rapid access to highly functionalized tricyclic scaffolds, including spirocyclic cyclohexadienones. Good yields and mild conditions are reported with high tolerance toward oxygen and water.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Cyclohexenes / chemical synthesis*
  • Cyclohexenes / chemistry
  • Molecular Structure
  • Oxygen / chemistry
  • Palladium / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Water / chemistry

Substances

  • Cyclohexenes
  • Spiro Compounds
  • cyclohexadienone
  • Water
  • Palladium
  • Oxygen