Transition Metal Catalyzed Grignard Cross-Coupling to Ortho-Halogenated Aryl Imines. An Efficient Synthesis of Ortho-Substituted Aryl Aldehydes

Article abstract of DOI:10.1021/jo00268a009

N-(o-Halogenated benzylidene)cyclohexylamines 2 were successfully reacted with reducing and nonreducing Grignard reagents in a transition metal catalyzed cross-coupling reaction resulting in an efficient single-step synthesis of ortho-substituted benzaldehydes after acidic workup.The dihalogenated benzylidene amines reacted regioselectively at the amine-activated ortho position to yield ortho-substituted halogenated benzaldehydes.