Intramolecular Arene C−H to C−P Functionalization Mediated by Nickel(II) and Palladium(II)

Abstract

A tris(phosphine) ligand with a triarylbenzene backbone was employed to support mono-nickel(II) and -palladium(II) complexes. Two phosphine arms coordinated to the metal center, while the third phosphine was found to form a C–P bond with dearomatization of the central arene. Deprotonation effected the rearomatization of the central ring and metal reduction from M(II) to M(0). The overall conversion corresponds to a functionalization of an unactivated arene C–H bond to a C–P bond. This transformation represents a rare type of mechanism of C–H functionalization, facilitated by the interactions of the group 10 metal with the arene π system. This conversion is reminiscent of and expands the scope of recently reported intramolecular rearrangements of biaryl phosphine ligands common in group 10 catalysis.

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