Visible-Light-Induced Direct Difluoroalkylation of Uracils, Pyridinones, and Coumarins

J Org Chem. 2017 Jan 20;82(2):910-917. doi: 10.1021/acs.joc.6b02316. Epub 2017 Jan 4.

Abstract

An efficient and general method for the synthesis of difluoroalkylated uracils, pyridinones, and coumarins through visible-light-induced reaction with commercial materials is developed. The strategy proceeds with high efficiency under mild reaction conditions and shows excellent functional group compatibility, even toward bromide and hydroxyl group, thus demonstrates high potent application in a late-stage fluoroalkylation. Moreover, the difluoroalkylated products can be further transformed to a diverse variety of difluoroalkylated heterocycles, including molecules of potential biological activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation / radiation effects
  • Coumarins / chemistry
  • Coumarins / metabolism*
  • Fluorine / chemistry*
  • Light*
  • Molecular Structure
  • Pyridones / chemistry
  • Pyridones / metabolism*
  • Uracil / chemistry
  • Uracil / metabolism*

Substances

  • Coumarins
  • Pyridones
  • Fluorine
  • Uracil