Fluorenone synthesis by palladacycle-catalyzed sequential reactions of 2-bromobenzaldehydes with arylboronic acids

Org Lett. 2011 May 6;13(9):2452-5. doi: 10.1021/ol200693d. Epub 2011 Apr 11.

Abstract

A new, anionic four-electron donor-based (type I) palladacycle-catalyzed sequential reaction of 2-bromobenzaldehydes with arylboronic acids based on the addition reaction, cyclization via C-H activation-oxidation sequence is described. Our study provided an efficient access to a variety of substituted fluorenones/indenofluorenediones from readily available arylboronic acids and 2-bromobenzaldehydes.

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

  • Benzaldehydes / chemistry*
  • Boronic Acids / chemistry*
  • Bromine Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Fluorenes / chemical synthesis*
  • Molecular Structure
  • Oxidation-Reduction
  • Palladium / chemistry*

Substances

  • Benzaldehydes
  • Boronic Acids
  • Bromine Compounds
  • Fluorenes
  • fluorene
  • Palladium