Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

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

Research output: Contribution to journalArticleResearchpeer-review

10 Citations (Scopus)

Abstract

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
Volume50
Issue number81
DOIs
Publication statusPublished - 2014
Externally publishedYes

Cite this