Journal
ACS CATALYSIS
Volume 10, Issue 21, Pages 12819-12827Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c03903
Keywords
cobalt; catalysis; benzonitriles; reductive cross-coupling; biaryl; cross-electrophile coupling
Categories
Funding
- CNRS
- Ecole Polytechnique
- OCCIGEN computational cluster of the CINES [A0070810977]
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Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds. Even though the cobalt catalyst is able to activate the C(sp(2))-CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, experimental insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative. Finally, density functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction.
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