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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Published inOrganic letters Vol. 26; no. 33; pp. 7055 - 7059
Main Authors Santana, Catherine G., Teoh, Yhin Sarah, Evarts, Madeline M., Shezaf, Jonathan Z., Krische, Michael J.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 23.08.2024
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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02642