Recent Advances in the Nickel‐catalysed Electrochemical Coupling Reactions with a Focus on the Type of Bond Formed

Abstract

Despite being around for many decades, electrochemical metal catalysis has recently widened the realm of electrochemical synthesis by merging sustainable electrosynthesis and tremendous metal catalysis. As the electric current can be controlled to stimulate the development of reactive intermediates and catalysts without the use of external oxidising or reducing agents and considering that it is more selective, generates less waste, and works under reasonable conditions, this strategy represents an eco-friendly and economically sustainable method. Nickel can be used efficiently in electrochemical metal-catalysed reactions owing to its inexpensive nature, high reactivity towards less reactive electrophiles and unique single electron transfer (SET) catalytic cycle. This review covers the recent advances in nickel-catalysed electrochemical coupling reactions from 2017 to 2022, with a focus on different reactions that forge CÀ C or C-heteroatom bonds.

Computational Methods Enable the Prediction of Improved Catalysts for Nickel-Catalyzed Cross-Electrophile Coupling

“…Heterocycle-based L2 dinitrogen ligands are critical enabling components of many transition-metal-catalyzed C–C, C–N, and C–O bond forming reactions. These ligandstypified by 2,2′-bipyridine (bpy)enable reactivity distinct from phosphine ligands by promoting a diverse set of one- and two-electron processes. − In particular, bpy ligands have become a fixture of nickel-catalyzed cross-electrophile, metallophotoredox, and electrochemical − couplings and are often the standard by which the reactivity of other ligands are gauged. The increased demand for more diverse bipyridine ligands can be observed in the surge of interest in substituted bipyridines (Figures A and S1.1).…”

Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

“…Generally, the carbon–chalcogen bond formation represents one of the most powerful methods to synthesize organochalcogen compounds and has been achieved by using transition-metal-catalyzed, photocatalyzed, electrochemical or metal-free protocols, etc. 7 A diversity of sulfur precursors, 8 including thiols, disulfides, sulfonyl hydrazides, and thiosulfonates, and selenium precursors 7 i ,9 such as diselenides and selenosulfonates have been frequently used as the thiolation/selenation sources in constructing the carbon–chalcogen bonds. As seen in an impressive recent study by Sun and coworkers, the selenosulfonate can even be used as both a selective sulfonylation and selenylation reagent for dienes to construct a diversity of sulfonyl benzo[ b ]-azepinones and seleno-benzo[ b ]azepines.…”

Recent Advances in Electrochemical, Ni‐Catalyzed C−C Bond Formation

“…[9] Mathew and coworkers reviewed Ni-catalyzed electrochemical CÀ C and CÀ heteroatom bond formations. [10] Ackermann and co-workers reviewed electrochemical, Ni-catalyzed CÀ H activation reactions that are reductive, redox-neutral, and oxidative. [11] Recent advances in Ni-catalyzed cross-coupling via paired electrolysis was reviewed by Li and co-workers.…”