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Issue 1, 2020
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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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Supplementary files

Article information


Submitted
21 Sep 2019
Accepted
01 Nov 2019
First published
01 Nov 2019

Org. Chem. Front., 2020,7, 19-24
Article type
Research Article

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

M. R. Sk and M. S. Maji, Org. Chem. Front., 2020, 7, 19
DOI: 10.1039/C9QO01164A

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