Aryne-Enabled C-N Arylation of Anilines

Thomas Sephton, Anastasios Charitou, Cristina Trujillo Del Valle, Jonathan M. Large, Sam Butterworth, Michael Greaney

Research output: Contribution to journalArticlepeer-review

Abstract

Anilines are potentially high-value arylating agents, but are limited by the low reactivity of the strong C-N bond. We show that the reactive intermediate benzyne can be used to both activate anilines, and set up an aryl transfer reaction in a single step. The reaction does not require any transition metal catalysts or stoichiometric organometallics, and establishes a metal-free route to valuable biaryl products by functionalizing the aniline C-N bond.
Original languageEnglish
Article numbere202310583
Number of pages7
JournalAngewandte Chemie. International Edition
Volume62
Issue number49
Early online date18 Oct 2023
DOIs
Publication statusPublished - 4 Dec 2023

Keywords

  • C−N arylation
  • Smiles rearrangement
  • aniline
  • aryne
  • biaryl synthesis

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