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

doi:10.1039/C1OB05365E

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Organic & Biomolecular Chemistry

Issue 14, 2011

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

Katie E. Judd and Lorenzo Caggiano

Org. Biomol. Chem., 2011,9, 5201-5210

DOI: 10.1039/C1OB05365E
Received 09 Mar 2011, Accepted 13 Apr 2011
First published on the web 15 Apr 2011

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Abstract
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Electron-rich aryl ethers and phenols react with isoprene (2-methylbuta-1,3-diene) in the presence of catalytic Bi(OTf)₃ at 40 °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.