Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

Ramesh Mudududdla, Rohit Sharma, Sheenu Abbat, Prasad V. Bharatam, Ram A. Vishwakarma, Sandip B. Bharate

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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.

Original languageEnglish
Pages (from-to)12076-12079
Number of pages4
JournalChemical Communications
Issue number81
Publication statusPublished - 2014
Externally publishedYes

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