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Oxidation of Olefins to Carbonyl Compounds: Modern View of the Classical Reaction

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Abstract

The results of 60 years' research into the mechanisms of olefin oxidation catalyzed by palladium complexes (Wacker oxidation) are analyzed. The concepts of the mechanisms of related oxidative carboxylations (Moiseev reaction) and alkoxylations are discussed. This review considers the regularities of processes in aqueous organic solvents; the problems of regio- and stereoselectivity of reactions; and the role of co-catalysts, oxidants, and ligands, including asymmetric catalysis. The effect of transition from anionic (or neutral) to cationic palladium chloride complexes in water or aqueous organic media on the mechanism of olefin oxidation is discussed in detail.

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ACKNOWLEDGMENTS

The author is grateful to Professors O.L. Kaliya, L.G. Bruk, and R.S. Shamsiev for useful comments and discussions of the review and to K. Egiazaryan (Russian Technological University) for the preparation of graphics for this review. My sincere gratitude is extended to the editorial board and the editors of Kinetics and Catalysis for many years of cooperation, which started with publication of my article (coauthored by V.K. Bykhovskii) On the Mechanism of Homogeneous Catalytic Activation of Hydrogen in the first volume of the journal (1960, no. 3).

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    O. N. Temkin

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Dedicated to Academician I. I. Moiseev, one of the founders of modern metal complex catalysis, on the occasion of his 90th birthday and 60th anniversary of the discovery of olefin oxidation

Translated by L. Smolina

Abbreviations: AA, acetaldehyde; anti-M, against Markovnikov rule; AAlc, allyl alcohols; APh, acetophenone; HV, hydrovinylation; HP, hydroxypalladation; HPA, heteropolyacid; DMA, acetaldehyde dimethylacetal; DEA, acetaldehyde diethylacetal; IL, ionic liquid; KIE, kinetic isotope effect; M, according to Markovnikov rule; MCI, metal-carbenium ion; PFCSs, polyfunctional catalytic systems; RS, regioselectivity; XRD, X-ray diffraction; PhI, phthalimide; ChH, chlorohydrin; CHex, cyclohexene; ECH, ethylene chlorohydrin; AIMD, ab initio molecular dynamics; AN, acetonitrile; BQ, p-benzoquinone; COD, cyclooctadiene-1,5; DFT, density functional theory; DMA, dimethylacetamide; DME, 1,2-dimethoxyethane; DMF, dimethylformamide; DMP, Dess–Martin periodinane; DMSO, dimethyl sulfoxide, NMP, N-methylpyrrolidone; Ox, oxidant; PcFe, iron phthalocyaninate complex; Q, quinone; THF, tetrahydrofuran; TMEDA, tetramethylethylenediamine; TOF, turnover frequency.

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Temkin, O.N. Oxidation of Olefins to Carbonyl Compounds: Modern View of the Classical Reaction. Kinet Catal 61, 663–720 (2020). https://doi.org/10.1134/S0023158420050122

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