<i>Cine-</i>Substitution of Enolates: Enolate Dance/Coupling of Cycloalkenyl Pivalates by Nickel Catalysis

Moriya, Eito; Muto, Kei; Yamaguchi, Junichiro

doi:10.1021/acscatal.4c02707

ACS Catal.

2024

DOI: 10.1021/acscatal.4c02707

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Cine-Substitution of Enolates: Enolate Dance/Coupling of Cycloalkenyl Pivalates by Nickel Catalysis

Eito Moriya,

Kei Muto,

Junichiro Yamaguchi

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Cited by 2 publications

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

Santana,

Teoh,

Evarts

et al. 2024

Org. Lett.

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

Santana,

Teoh,

Evarts

et al. 2024

Org. Lett.

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show abstract

Nickel-Catalyzed Cine-Substitution of Enolates

2024

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Cine-Substitution of Enolates: Enolate Dance/Coupling of Cycloalkenyl Pivalates by Nickel Catalysis

Cited by 2 publications

References 55 publications

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

Nickel-Catalyzed Cine-Substitution of Enolates

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