☆ 4.6 Article

Vanadyl species-catalyzed complementary β-oxidative carbonylation of styrene derivatives with aldehydes

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY

卷 13, 期 8, 页码 2385-2392

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ROYAL SOC CHEMISTRY

DOI: 10.1039/c4ob02621g

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Chemistry, Organic

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Ministry of Science of Technology of Taiwan [NSC 101-2113-M-007-009-MY3]

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A series of oxometallic species and metal acetylacetonates (acac) was examined as catalysts for oxidative carbonylation of styrene with benzaldehyde using t-butylhydroperoxide as the co-oxidant in warm acetonitrile. Among them, VO((acac)(2) and vanadyl(IV) chloride were found to be the only catalyst class to achieve cross-coupling processes by judiciously tuning the ligand electronic attributes, leading to beta-hydroxylation- and beta-peroxidation-carbonylation of styrene, respectively, in a complementary manner. Mechanistic studies indicated that vanadyl-associated acyl radicals generated by t-butoxy radical-assisted, homolytic cleavage of the aldehyde C-H bond were involved in tandem processes with an exclusive syn diastereoselectivity in the case of beta-methylstyrene.

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