Visible-Light- and PPh<sub>3</sub>-Mediated Direct C–N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature
Kartic Manna, Tanusree Ganguly, Sujoy Baitalik, Ranjan Jana
Abstract
We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.
Topics & Concepts
ChemistryNitreneAminationArylAlkylBoronic acidTriphenylphosphinePhotochemistryReductive aminationCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisCatalytic Cross-Coupling ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods