Aryne‐Enabled C−N Arylation of Anilines
Thomas Sephton, Anastasios Charitou, Cristina Trujillo, Jonathan M. Large, Sam Butterworth, Michael F. Greaney
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.
Topics & Concepts
AryneAnilineChemistryArylStoichiometryCatalysisReactivity (psychology)Combinatorial chemistryReactive intermediateTransition metalComputational chemistryOrganic chemistryMedicinal chemistryAlternative medicineAlkylPathologyMedicineCyclization and Aryne ChemistryCatalytic Alkyne ReactionsChemical Reactions and Mechanisms