Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen-Radicals

Research output: Contribution to journalArticle

  • Authors:
  • Sara Morcillo
  • Elizabeth Dauncey
  • Ji Hye Kim
  • James J. Douglas
  • Nadeem S Sheikh
  • And 1 others
  • External authors:
  • Daniele Leonori

Abstract

The selective functionalization of C(sp3)−H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5‐H‐atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late‐stage functionalization of amino acids and a dipeptide.

Bibliographical metadata

Original languageEnglish
Pages (from-to)12945-12949
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number39
Early online date3 Aug 2018
DOIs
Publication statusPublished - 19 Sep 2018