Oxidation by cobalt(<scp>III</scp>) acetate. Part 10. Effects of ring substituents on the product distributions in the oxidation of β-methylstyrenes by cobalt(<scp>III</scp>) acetate in acetic acid

gem-Difluoroalkenes represent valuable synthetic handles for organofluorine chemistry; however, most reactions of this substructure proceed through reactive intermediates prone to eliminate a fluorine atom and generate monofluorinated products. Taking advantage of the distinct reactivity of gem-difluoroalkenes, we present a cobalt-catalyzed regioselective unsymmetrical dioxygenation of gem-difluoroalkenes using phenols and molecular oxygen, which retains both fluorine atoms and provides β-phenoxy-β,β-difluorobenzyl alcohols. Mechanistic studies suggest that the reaction operates through a radical chain process initiated by Co(II)/O2/phenol and quenched by the Co-based catalyst. This mechanism enables the retention of both fluorine atoms, which contrasts most transition-metal-catalyzed reactions of gem-difluoroalkenes that typically involve defluorination.

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Oxidation by cobalt(III) acetate. Part 10. Effects of ring substituents on the product distributions in the oxidation of β-methylstyrenes by cobalt(III) acetate in acetic acid

Cited by 4 publications

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ChemInform Abstract: Oxidation by Cobalt(III) Acetate. Part 10. Effects of Ring Substituents on the Product Distributions in the Oxidation of β‐Methylstyrenes by Cobalt(III) Acetate in Acetic Acid.

ChemInform Abstract: Oxidation by Cobalt(III) Acetate. Part 10. Effects of Ring Substituents on the Product Distributions in the Oxidation of β‐Methylstyrenes by Cobalt(III) Acetate in Acetic Acid.

Phytochemical and chemotaxonomic investigations on the fruit parts of Illicium verum Hook. f

Cobalt-Catalyzed Selective Unsymmetrical Dioxidation of gem-Difluoroalkenes

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