Nickel-catalyzed, silyl-directed, ortho-borylation of arenes via an unusual Ni(II)/Ni(IV) catalytic cycle

Xiaoshi Su, Guoao Li, Linke He, Shengda Chen, Xiaoliang Yang, Guoqiang Wang () and Shuhua Li ()
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Xiaoshi Su: Nanjing University
Guoao Li: Nanjing University
Linke He: Nanjing University
Shengda Chen: Nanjing University
Xiaoliang Yang: Nanjing University
Guoqiang Wang: Nanjing University
Shuhua Li: Nanjing University

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract Nickel-catalyzed C–H bond functionalization reactions provide an impressive alternative to those with noble metal catalysts due to their unique reactivity and low cost. However, the regioselective C(sp2)–H borylation reaction of arenes accomplished by nickel catalyst remains limited. We herein disclose a silyl-directed ortho C(sp2)–H borylation of substituted arenes with a Ni(cod)2/PMe3/KHMDS catalyst system. Using readily available starting materials, this protocol provides easy access to ortho-borylated benzylic hydrosilanes bearing flexible substitution patterns. These products can serve as versatile building blocks for the synthesis of sila or sila/borine heterocycles under mild conditions. Control experiments and DFT calculations suggest that a catalytic amount of base prompts the formation of Ni(II)-Bpin-ate complex, likely related to the C(sp2)–H bond activation. This borylation reaction might follow an unusual Ni(II)/Ni(IV) catalytic cycle.

Date: 2024
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DOI: 10.1038/s41467-024-51997-0

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