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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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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