Regioselective Pd-catalyzed aerobic aza-Wacker cyclization for preparation of isoindolinones and isoquinolin-1(2H)-ones

Org Lett. 2012 Jan 6;14(1):268-71. doi: 10.1021/ol203043h. Epub 2011 Dec 8.

Abstract

A switchable regioselective intramolecular aerobic aza-Wacker cyclization catalyzed by palladium is presented. Isoindolinones or isoquinolin-1(2H)-ones could be prepared selectively from the same substrates using different catalysts. The type and steric hindrance of the ligands may be the variables most significant for regiocontrol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Isoindoles / chemical synthesis*
  • Isoquinolines / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Aza Compounds
  • Isoindoles
  • Isoquinolines
  • Palladium
  • Oxygen