Evolution of High‐Valent Nickela‐Electrocatalyzed C−H Activation: From Cross(‐Electrophile)‐Couplings to Electrooxidative C−H Transformations

Abstract

Abstract C−H activation has emerged as one of the most efficient tools for the formation of carbon–carbon and carbon–heteroatom bonds, avoiding the use of prefunctionalized materials. In spite of tremendous progress in the field, stoichiometric quantities of toxic and/or costly chemical redox reagents, such as silver(I) or copper(II) salts, are largely required for oxidative C−H activations. Recently, electrosynthesis has experienced a remarkable renaissance that enables the use of storable, safe and waste‐free electric current as a redox equivalent. While major recent momentum was gained in electrocatalyzed C−H activations by 4d and 5d metals, user‐friendly and inexpensive nickela‐electrocatalysis has until recently proven elusive for oxidative C−H activations. Herein, the early developments of nickela‐electrocatalyzed reductive cross‐electrophile couplings as well as net‐redox‐neutral cross‐couplings are first introduced. The focus of this Minireview is, however, the recent emergence of nickel‐catalyzed electrooxidative C−H activations until April 2020.

Go electro! Nickela‐electrocatalyzed C−H activations have emerged as a sustainable platform in molecular sciences that avoid substrate prefunctionalizations and chemical oxidants by electricity. The robust nickela‐electrooxidations enabled C−C, C−O, and C−N formations with ample scope under exceedingly mild conditions. image