From alcohols to indoles: a tandem Ru catalyzed hydrogen-transfer Fischer indole synthesis

Org Lett. 2012 Dec 7;14(23):6112-5. doi: 10.1021/ol3030956. Epub 2012 Nov 28.

Abstract

In a new version of the Fischer indole synthesis, primary and secondary alcohols have been catalytically oxidized in the presence of phenylhydrazines and protic or Lewis acids to give the corresponding indoles. The overall reaction can be accomplished in one step, and the use of alcohols instead of aldehyes or ketones as starting materials has several advantages in terms of a large selection of reagents, easy handling, and safety of the process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Catalysis
  • Hydrogen / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Phenylhydrazines / chemistry*
  • Ruthenium / chemistry*

Substances

  • Alcohols
  • Indoles
  • Phenylhydrazines
  • Ruthenium
  • Hydrogen