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The mechanism of the reductive homocoupling of pyridine derivatives mediated by the Zr II synthon [(PNP)Zr(η 6 -toluene)Cl] ( 1 ) has been investigated. Selective transformation into three different types of product complexes has been observed, depending on the N-heterocyclic substrate employed: the bipyridyl complexes 3-R (R = Me, Et,  t  Bu, Bn, Ph, CHCHPh), which are the homocoupling products, the η 2 -((4-dimethylamino)pyridyl) complex 4 as well as the bis(isoquinolinyl) complex 5 . By deuterium labelling experiments the participation of the ligand backbone in the pyridine coupling reaction via potential cyclometallation steps was ruled out. Based on DFT modelling of the possible reaction sequences a reaction mechanism for the coupling sequence could be identified. The latter is initiated by a reductive syn C-C coupling rather than based on an initial C-H activation of the pyridine substrate.

Dehydrogenative coupling of 4-substituted pyridines mediated by a zirconium(ii) synthon: reaction pathways and dead ends