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Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals

Cam-Van T. Vo, T. Andrew Mitchell and Jeffrey W. Bode*

*Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, Wolfgang Pauli Strasse 10, 8093 Zürich, Switzerland, Email: bodeorg.chem.ethz.ch

C.-V. T. Vo, T. A. Mitchell, J. W. Bode, J. Am. Chem. Soc., 2011, 133, 14082-14089.

DOI: 10.1021/ja205174c (free Supporting Information)


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Abstract

Mixed acetals and organotrifluoroborates undergo BF3·OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF3·OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates.

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Key Words

ethers


ID: J48-Y2011-2460