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Issue 8, 2015
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Vanadyl species-catalyzed complementary β-oxidative carbonylation of styrene derivatives with aldehydes

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Abstract

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 β-hydroxylation– and β-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 β-methylstyrene.

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

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Publication details

The article was received on 18 Dec 2014, accepted on 18 Dec 2014 and first published on 18 Dec 2014


Article type: Paper
DOI: 10.1039/C4OB02621G
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Citation: Org. Biomol. Chem., 2015,13, 2385-2392

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

    W. Yang, S. Weng, A. Ramasamy, G. Rajeshwaren, Y. Liao and C. Chen, Org. Biomol. Chem., 2015, 13, 2385
    DOI: 10.1039/C4OB02621G

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