Bi(OTf)3-catalysed prenylation of electron-rich aryl ethers and phenols with isoprene: a direct route to prenylated derivatives

Katie E Judd, Lorenzo Caggiano

Research output: Contribution to journalArticle

13 Citations (Scopus)
285 Downloads (Pure)

Abstract

Electron-rich aryl ethers and phenols react with isoprene (2-methylbuta-1,3-diene) in the presence of catalytic Bi(OTf)(3) at 40 degrees C to afford the corresponding prenylated or 2,2-dimethylchroman products, respectively, in moderate to good yields. This transformation offers a convenient and expedient entry to prenylated derivatives of electron-rich aromatics that often display enhanced biological activities. The methodology has been employed in the efficient synthesis of a biologically active natural product and related compounds.
Original languageEnglish
Pages (from-to)5201-5210
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number14
Early online date14 Apr 2011
DOIs
Publication statusPublished - 21 Jul 2011

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