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Cobalt(iii)-catalyzed ketone-directed C–H vinylation using vinyl acetate

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Abstract

Weakly coordinating, ketone-directed C–H vinylation using vinyl acetate is reported here for a wide range of aromatic ketones such as acetophenones, diaryl ketones, chromones and biologically relevant chalcones under cost-effective and air-stable cobalt(III)-catalysis. Regioselective, mono-vinylation occurs for challenging vinyl substitution-free styrenes in moderate to good yields, and this moiety has been used to synthesize functionalized indanone, α-naphthol and an advanced intermediate for bruguierol A synthesis. An acrylate-surrogate provided the corresponding alkenylated product under these vinylation conditions. Detailed mechanistic studies are carried out to support the proposed catalytic cycle.

Graphical abstract: Cobalt(iii)-catalyzed ketone-directed C–H vinylation using vinyl acetate

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Publication details

The article was received on 21 Sep 2019, accepted on 01 Nov 2019 and first published on 01 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01164A
Org. Chem. Front., 2019, Advance Article

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    Cobalt(III)-catalyzed ketone-directed C–H vinylation using vinyl acetate

    M. R. Sk and M. S. Maji, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01164A

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