Modular o-quinone catalyst system for dehydrogenation of tetrahydroquinolines under ambient conditions

J Am Chem Soc. 2014 Aug 27;136(34):11910-3. doi: 10.1021/ja506546w. Epub 2014 Aug 19.

Abstract

Quinolines are common pharmacophores present in numerous FDA-approved pharmaceuticals and other bioactive compounds. Here, we report the design and development of new o-quinone-based catalysts for the oxidative dehydrogenation of tetrahydroquinolines to afford quinolines. Use of a Co(salophen) cocatalyst allows the reaction to proceed efficiently with ambient air at room temperature. The utility of the catalytic method is demonstrated in the preparation of a number of medicinally relevant quinolines.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry*
  • Hydrogenation
  • Molecular Structure
  • Oxidation-Reduction
  • Quinolines / chemistry*
  • Quinones / chemistry*
  • Ruthenium / chemistry*
  • Time Factors

Substances

  • Coordination Complexes
  • Quinolines
  • Quinones
  • Ruthenium
  • 1,2,3,4-tetrahydroquinoline