From Styrenes to Fluorinated Benzyl Bromides: A Photoinduced Difunctionalization via Atom Transfer Radical Addition

Org Lett. 2022 Jul 8;24(26):4750-4755. doi: 10.1021/acs.orglett.2c01699. Epub 2022 Jun 29.

Abstract

An operationally simple and practical method is disclosed to achieve the difunctionalization of styrenes, generating fluorinated benzyl bromides via a photoinduced atom transfer radical addition process. The developed method is mild, atom-economical, cost-effective, employs very low photocatalyst loading (1000 ppm), and is highly compatible with a broad range of functional groups on styrene. The versatility of the fluorinated benzyl bromides is demonstrated through their derivatization to a variety of valuable compounds.

Publication types

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

MeSH terms

  • Benzyl Compounds
  • Bromides*
  • Catalysis
  • Styrenes*

Substances

  • Benzyl Compounds
  • Bromides
  • Styrenes
  • benzyl bromide