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Issue 32, 2016

Temperature-controlled redox-neutral ruthenium(ii)-catalyzed regioselective allylation of benzamides with allylic acetates

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Abstract

Substituted aromatic amides reacted efficiently with allylic acetates in the presence of a cationic ruthenium complex in ClCH2CH2Cl at room temperature providing ortho allylated benzamides in a highly regioselective manner without any oxidant and base. The whole catalytic reaction occurred in a Ru(II) oxidation state and thus the oxidation step is avoided. By tuning the reaction temperature, ortho allyl and vinyl benzamides were prepared exclusively. Later, ortho allyl and vinylated benzamides were converted into biologically useful six- and five-membered benzolactones in the presence of HCl.

Graphical abstract: Temperature-controlled redox-neutral ruthenium(ii)-catalyzed regioselective allylation of benzamides with allylic acetates

Supplementary files

Article information


Submitted
10 Jun 2016
Accepted
14 Jul 2016
First published
14 Jul 2016

Org. Biomol. Chem., 2016,14, 7691-7701
Article type
Paper

Temperature-controlled redox-neutral ruthenium(II)-catalyzed regioselective allylation of benzamides with allylic acetates

R. Manikandan and M. Jeganmohan, Org. Biomol. Chem., 2016, 14, 7691 DOI: 10.1039/C6OB01498D

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