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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

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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 °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.

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

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Publication details

The article was received on 09 Mar 2011, accepted on 13 Apr 2011 and first published on 15 Apr 2011


Article type: Paper
DOI: 10.1039/C1OB05365E
Org. Biomol. Chem., 2011,9, 5201-5210

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

    K. E. Judd and L. Caggiano, Org. Biomol. Chem., 2011, 9, 5201
    DOI: 10.1039/C1OB05365E

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