Tandem reduction and trifluoroethylation of quinolines and quinoxalines with trifluoroacetic acid and trimethylamine borane

Org Biomol Chem. 2022 Dec 14;20(48):9613-9617. doi: 10.1039/d2ob01923j.

Abstract

A metal-free tandem reduction and N-trifluoroethylation of quinolines and quinoxalines has been developed. It provided a convenient route to access trifluoroethylated tetrahydroquinolines and tetrahydroquinoxalines. This one-pot method avoids the purification process of the intermediate. Mechanistically, the in situ-generated boryl acetal species reacted with tetrahydroquinolines to generate iminiums followed by reduction to give the target compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes*
  • Quinolines*
  • Quinoxalines
  • Trifluoroacetic Acid

Substances

  • Boranes
  • Quinoxalines
  • Trifluoroacetic Acid
  • trimethylamine
  • Quinolines