δ-C-H Halogenation Reactions Enabled by a Nitrogen-Centered Radical Precursor

Org Lett. 2022 May 27;24(20):3652-3656. doi: 10.1021/acs.orglett.2c01261. Epub 2022 May 13.

Abstract

Nitrogen-centered radicals are versatile synthetic intermediates with the ability to undergo diverse reactions such as hydrogen atom transfer (HAT), β-scission, and addition across unsaturated systems. A long-standing impediment to the wider adoption of these intermediates in synthesis has been the difficulty of their generation. Herein we disclose a new hydrazonyl carboxylic acid precursor to nitrogen-centered radicals and its application toward remote C-H fluorination and chlorination reactions of sulfonyl-protected alkyl amines via 1,5-HAT.

Publication types

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

MeSH terms

  • Amines
  • Halogenation*
  • Hydrogen
  • Nitrogen*

Substances

  • Amines
  • Hydrogen
  • Nitrogen