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Issue 2, 2014
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Indium(III) triflate-catalysed [4 + 2] benzannulation reactions of o-alkynylbenzaldehydes with enolisable carbonyl compounds: selective synthesis of naphthyl ketones

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Abstract

Indium(III) triflate is found to be an effective catalyst for the benzannulation reactions of o-alkynylbenzaldehydes with enolisable aldehydes, ketones, 1,3-diketones and β-keto esters. The reactions produce naphthyl ketones through ring opening of adducts arising from the inverse electron demand Diels–Alder reactions between in situ generated isochromenylium cations and enols. The main feature of the method is selective formation of naphthyl ketones in a highly regioselective manner without any decarbonylation.

Graphical abstract: Indium(iii) triflate-catalysed [4 + 2] benzannulation reactions of o-alkynylbenzaldehydes with enolisable carbonyl compounds: selective synthesis of naphthyl ketones

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Publication details

The article was received on 12 Jul 2013, accepted on 03 Oct 2013 and first published on 03 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41439F
Citation: Org. Biomol. Chem., 2014,12, 269-277
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    Indium(III) triflate-catalysed [4 + 2] benzannulation reactions of o-alkynylbenzaldehydes with enolisable carbonyl compounds: selective synthesis of naphthyl ketones

    K. Sakthivel and K. Srinivasan, Org. Biomol. Chem., 2014, 12, 269
    DOI: 10.1039/C3OB41439F

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