Regioselective Metal-Free Cross-Coupling of Quinoline N-Oxides with Boronic Acids

Org Lett. 2015 Jun 19;17(12):3134-7. doi: 10.1021/acs.orglett.5b01456. Epub 2015 Jun 11.

Abstract

A novel and operationally simple one-step C-H bond functionalization of quinoline N-oxides to 2-substituted quinolines was developed. This approach enables the regioselective functionalization under external oxidant- and metal-free conditions. The developed transformation represents the first application of the Petasis reaction in functionalization of heterocycles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry*
  • Catalysis
  • Cyclic N-Oxides / chemistry*
  • Hydrogen Bonding
  • Metals / chemistry*
  • Molecular Structure
  • Oxidants / chemistry
  • Quinolines / chemistry*

Substances

  • Boronic Acids
  • Cyclic N-Oxides
  • Metals
  • Oxidants
  • Quinolines