Nickel-Catalyzed C-Heteroatom Cross-Coupling Reactions under Mild Conditions via Facilitated Reductive Elimination

The formation of C-heteroatom bonds represents an important type of bond-forming reaction in organic synthesis and often provides a fast and efficient access to privileged structures found in pharmaceuticals, agrochemical and materials. In contrast to conventional Pd- or Cu-catalyzed C-heteroatom cross-couplings under high-temperature conditions, recent advances in homo- and heterogeneous Ni-catalyzed C-heteroatom formations under mild conditions are particularly attractive from the standpoint of sustainability and practicability. The generation of Ni-III and excited Ni-II intermediates facilitate the reductive elimination step to achieve mild cross-couplings. This review provides an overview of the state-of-the-art approaches for mild C-heteroatom bond formations and highlights the developments in photoredox and nickel dual catalysis involving SET and energy transfer processes; photoexcited nickel catalysis; electro and nickel dual catalysis; heterogeneous photoredox and nickel dual catalysis involving graphitic carbon nitride (mpg-CN), metal organic frameworks (MOFs) or semiconductor quantum dots (QDs); as well as more conventional zinc and nickel dual catalyzed reactions.

Automated summary

The formation of C-heteroatom bonds through recent advances in homo- and heterogeneous Ni-catalyzed reactions under mild conditions is attractive due to sustainability and practicability. The generation of Ni-III and excited Ni-II intermediates enables mild cross-couplings, leading to the development of various catalytic systems involving photoredox and nickel dual catalysis, photoexcited nickel catalysis, electro and nickel dual catalysis, and heterogeneous photoredox and nickel dual catalysis using different materials.