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

---

see article for more reactions

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.

see article for more examples

---

---

Key Words

ethers

---

ID: J48-Y2011-2460