Mechanism of the Nickel-Catalyzed Electrosynthesis of Ketones by Heterocoupling of Acyl and Benzyl Halides

Syntheses and properties of molecular nickel(II) hydride, methyl, and nickel(I) complexes supported by trimethylphosphane and (2-diphenylphosphanyl)thiophenolato and -naphtholato ligands

“…The monovalent oxidation state of nickel has received increasing attention in recent years, in part due to its active role in a number of catalytic processes including biochemical reactions [26][27][28][29][30][31][32][33][34][35][36][37][38][39]40], nickel mediated cross-coupling reactions to make new C-C bonds [39,[40][41][42][43][44][45][46], alkene oligomerization by heterogeneous [47][48][49][50][51][52][53][54][55][56][57][58][59][60] and homogeneous nickel catalysts [61][62], and other processes [63][64][65][66][67]. We hope that the results presented here will help to appreciate the role of Ni(I) in these processes.…”

Electron transfer in organonickel complexes of α-diimines: Versatile redox catalysts for C–C or C–P coupling reactions – A review

“…A mechanism for the C-C coupling reactions was initially proposed by Amatore and Jutand for corresponding diphosphine (dppe) complexes and the formation of biaryl from aryl halides ArX (Scheme 2) [10,[24][25][26]. Under the reductive conditions the Ni(II) precursor complexes were successively reduced to Ni(0).…”

“…Homogeneous catalysis has been increasingly used since it can offer valuable advantages, notably in terms of selectivity and efficiency. Electrochemistry is connected to this field in many ways [4][5][6][7][8][9][10]. Electrochemical methods enable one to synthesise many organometallic compounds, study the reactivity of coordination compounds and elucidate possible reaction mechanisms.…”

“…Electrochemical methods enable one to synthesise many organometallic compounds, study the reactivity of coordination compounds and elucidate possible reaction mechanisms. In recent years, the use of electrochemically generated catalysts in reactions of organic compounds has assumed great importance both in organic synthesis and in thorough investigations into electron transfer, bond cleavage, substitution, addition and other reactions [4][5][6][7][8][9][10][11][12][13][14][15][16][17].…”

Carbon−Carbon Bond Formation with Electrogenerated Nickel and Palladium Complexes

“…The mechanism of this nickel-catalysed electrosynthesis of ketones has been examined in the case of the coupling of benzoyl chloride with benzyl bromide. [216] The electrogenerated Ni 0 complex added oxidatively to benzyl bromide, and the resulting Ni II complex was further reduced at the potential of the Ni II /Ni 0 reduction. The reduced complex reacted with benzoyl chloride to generate the ketone coupling product.…”