Palladium-catalyzed direct arylation of 5-chloropyrazoles: a selective access to 4-aryl pyrazoles

J Org Chem. 2012 Sep 7;77(17):7659-64. doi: 10.1021/jo301047v. Epub 2012 Aug 21.

Abstract

The use of a temporary protection by a chloro group at C5 of pyrazoles allows the synthesis of the 4-arylated pyrazoles, which were previously inaccessible by palladium-catalyzed direct arylation, with complete regioselectivity and in high yields using in most cases as little as 0.5-0.1 mol % Pd(OAc)(2) as the catalyst with electron-deficient aryl bromides. Moreover, from 5-chloro-1,3-dimethylpyrazole, sequential catalytic C4 arylation, dechlorination, catalytic C5 arylation reactions allowed the synthesis of a 4,5-diarylated pyrazole derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry

Substances

  • Organometallic Compounds
  • Pyrazoles
  • Palladium