Formate-Mediated Reductive Cross-Coupling of Vinyl Halides and Aryl Iodides: cine-Substitution via Palladium(I) Catalysis

Formate-Mediated Reductive Cross-Coupling of Vinyl Halides and Aryl Iodides: cine-Substitution via Palladium(I) Catalysis

Formate-mediated reductive cross-couplings of vinyl halides with aryl iodides via palladium­(I) catalysis occur with highly uncommon cine-substitution. The active dianionic palladium­(I) catalyst, [Pd2I4]­[NBu4]2, is generated in situ from Pd­(OAc)2, Bu4NI, and formate. Oxidative addition of aryl io...

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Veröffentlicht in:Organic letters 2024-08, Vol.26 (33), p.7055-7059
Hauptverfasser: Santana, Catherine G., Teoh, Yhin Sarah, Evarts, Madeline M., Shezaf, Jonathan Z., Krische, Michael J.
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container_issue 33
container_start_page 7055
container_title Organic letters
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creator Santana, Catherine G.
Teoh, Yhin Sarah
Evarts, Madeline M.
Shezaf, Jonathan Z.
Krische, Michael J.
description Formate-mediated reductive cross-couplings of vinyl halides with aryl iodides via palladium­(I) catalysis occur with highly uncommon cine-substitution. The active dianionic palladium­(I) catalyst, [Pd2I4]­[NBu4]2, is generated in situ from Pd­(OAc)2, Bu4NI, and formate. Oxidative addition of aryl iodide followed by dissociation of the dimer provides the monomeric anionic T-shaped arylpalladium­(II) species, [Pd­(Ar)­(I)2(NBu4)], which, upon vinyl halide carbopalladation, forms products of cine-substitution by way of palladium­(IV) carbenes, as corroborated by deuterium-labeling experiments.
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