While metathesis reactions involving carbon−carbon double bonds, namely olefin metathesis, has been well established with broad utilities in organic synthesis and material science, direct metathesis of strong C−C single bonds has been extremely rare. Here, we report a ruthenium-catalyzed reversible C−C single-bond metathesis reaction that allows redox- and pH-neutral biaryl synthesis. Assisted by directing groups, unstrained homo-biaryl compounds undergo aryl exchanges to generate cross-biaryl products, catalyzed by a well-defined air-stable ruthenium(II) complex. Functional groups reactive under typical cross-coupling reactions, such as halogen, silyl, and boronate moieties, are compatible under the metathesis conditions. Mechanistic studies disclose an intriguing “olefin-metathesis-like” pathway, which involves a surprising heptacoordinated, 18-electron close-shell intermediate. The distinct reaction mode discovered here is expected to inspire the development of more general C−C single-bond metathesis and orthogonal cross-coupling reactions.

C-C single bond metathesis

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ACS Fall 2022

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