Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles

J Org Chem. 2007 Feb 16;72(4):1476-9. doi: 10.1021/jo061979v.

Abstract

This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.

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
  • Indoles / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Phosphines
  • Pyrroles / chemistry*

Substances

  • Indoles
  • Phosphines
  • Pyrroles
  • Palladium