Activation of the carbonnickel σ-bond by cathodic reduction of trans-bromo-bis(triphenylphosphine)phenylnickel(II) in the presence of triphenylphosphine

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Abstract

The complex trans-[Ni(PPh3)2(Ph)Br] is found to be cathodically reduced in two steps in acentonitrile solution containing free PPh3 at a platinum electrode. Both processes cause the activation of the σ- bonded organic group and the consequent formation of biphenyl along two quite different reaction pathways. In the first one the coupling product simply arises from the collapse of the metallorganic nickel(I) complex cathodicall generated; in the second step biphenyl is formed in reaction between a very reactive electrogenerated organometallic nickel(0) species and the parent nickel(II) complex.

Unambigiuous evidences of the occurence of eletrocatalyzed homo- and hetero-coupling are obtained when the cathodic reductions of the title complex are carried out in the presence of bromobenzene and benzyl chloride.

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