4 years ago

A 1,2-Addition Pathway for C(sp2)−H Activation at a Dinickel Imide

A 1,2-Addition Pathway for C(sp2)−H Activation at a Dinickel Imide
Eric J. Schelter, Kimberly C. Mullane, Cholpisit Kiattisewee, Christopher Uyeda, Ian G. Powers
A dinickel imido complex was synthesized using a redox-active naphthyridine-diimine supporting ligand. Upon coordination of an external ligand, the Ni2 core was disrupted, triggering an aromatic C−H activation reaction to generate a Ni2(μ-NHAr)(Ar) species. This intermediate is capable of liberating free carbazole and phenanthridine products upon heating or treatment with excess tBuNC. Collectively, these studies establish a kinetically facile 1,2-addition mechanism for C(sp2)−H activation, taking advantage of cooperative reactivity between two Ni centers. Cooperative reactivity: An isolable dinickel nitrene complex is shown to activate aromatic C−H bonds by a 1,2-addition mechanism. Heterocyclic products can be liberated from the C−H activated intermediate through thermal or ligand-induced reductive elimination.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701855

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