meta-C–H Arylation of fluoroarenes via traceless directing group relay strategy

Research output: Contribution to journalArticle

  • Authors:
  • Marc Font
  • Andrew Spencer
  • Igor Larrosa

Abstract

While several methods are now available for the ortho and selective arylation of fluoroarenes, meta-functionalisation has never been achieved. We report a new methodology, based on the traceless directing group relay concept, leading to the first meta-selective (hetero)arylation of fluoroarenes. In this strategy, CO2 is introduced as a transient directing group, to control a Pd-catalyzed arylation meta to the fluoro functionality, prior to its release in a sequential, one-pot fashion. This method has shown compatibility with a number of functional groups and substitution patterns in both the fluoroarene core and aryl iodide coupling partners, and proceeds with complete meta-selectivity and mono vs bis-arylation selectivity.

Bibliographical metadata

Original languageEnglish
JournalChemical Science
Early online date25 Jul 2018
DOIs
Publication statusPublished - 2018