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Issue 81, 2014
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Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

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A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C–C bond cleavage followed by intermolecular [4+2]-Diels–Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist.

Graphical abstract: Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

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Publication details

The article was received on 04 Jul 2014, accepted on 18 Aug 2014 and first published on 18 Aug 2014

Article type: Communication
DOI: 10.1039/C4CC05151C
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2014,50, 12076-12079
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    Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

    R. Mudududdla, R. Sharma, S. Abbat, P. V. Bharatam, R. A. Vishwakarma and S. B. Bharate, Chem. Commun., 2014, 50, 12076
    DOI: 10.1039/C4CC05151C

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