Chem
Volume 6, Issue 5, 14 May 2020, Pages 1056-1081
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Review
Nickel-Catalyzed C−H Functionalization Using A Non-directed Strategy

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The Bigger Picture

The formation of C–C bonds via C–H bond activation has great significance in the field of organic synthesis because it provides an ideal route to the production of valuable chemical compounds. The overall reaction reduces the number of synthetic steps and minimizes by-product formation, thus rendering C–H functionalization environmentally benign and economically attractive. Direct C–H functionalization strategies can facilitate and expedite the synthesis of naturally occurring compounds, biologically active compounds, agriculturally important products, pharmaceutical drug molecules, as well as functional materials. Although various transition-metal complexes can be used as catalysts, nickel-catalyzed C–H activation has become a predominant and ubiquitous research area in organic chemistry because nickel is an abundant, inexpensive metal with unique catalytic activity.

Summary

The activation of ubiquitous C–H bonds has great significance in the field of organic synthesis given that it represents an ideal method for directly producing valuable chemicals from structurally simple compounds. First-row transition metals have recently been recognized as a potential alternative to noble transition metals because of their low cost, unique reactivity profiles, and easy availability. Among these metals, nickel (Ni) catalysts have drawn considerable attention from the scientific community. This review focuses on Ni-catalyzed C–H functionalization reactions of (hetero)arenes, including alkylation, arylation, alkenylation, alkynylation, borylation, and trifluoromethylation by using non-directing group strategies. In addition, mechanistic aspects of Ni-catalyzed C–H functionalization reactions are discussed because this allows possible new insights into catalyst improvement.

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Keywords

C–H activation
C–H functionalization
nickel
non-directed
C–C bond formation

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