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Synfacts 2024; 20(11): 1155
DOI: 10.1055/s-0043-1775179
Metals in Synthesis

Silyl-Directed Borylative C–H Functionalization of Arenes

Contributor(s):
Mark Lautens
,
Alexa Torelli
Su X, Li G, He L, Chen S, Yang X, Wang G, *, Li S. * Nanjing University, P. R. of China
Nickel-Catalyzed, Silyl-Directed, ortho-Borylation of Arenes via an Unusual Ni(II)/Ni(IV) Catalytic Cycle.

Nat. Commun. 2024;
15: 7549
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Key words

nickel catalysis - borylation - ortho-functionalization

Significance

A nickel-catalyzed silyl-directed ortho-C(sp²)–H borylation of substituted arenes is reported. The reaction utilizes readily accessible reagents, and the products contain both a hydro­silane and a boronate moiety, allowing for further functionalization.


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Comment

The methodology can be applied to a range of arenes, including drug-relevant substrates. Experimental and computational studies support a two-electron pathway, involving the generation of a reactive Ni(II)–Bpin-ate intermediate (I). Oxidative addition of B2pin2 forms the six-membered nickel species IV.


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Publication History

Article published online:
16 October 2024

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