Cascade amination and acetone monoarylation with aryl iodides by palladium/norbornene cooperative catalysis

Abstract

A palladium/norbornene cocatalyzed three-component reaction of aryl iodides, O-benzoylhydroxylamines, and acetone is reported. o′-Aminoaryl acetones or o,o′-diaminoaryl acetones are efficiently prepared via tandem ortho-C-H amination/ipso-C-I α-arylation sequence, and the regiospecificity has been confirmed by X-ray analysis. The proposed method addresses the condensation/amination of free-N-H-bearing substrates in acetone monoarylations and the synthesis of extremely congested 2,6-disubstituted aryl acetones.