4.8 Article

Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 4, Pages 1202-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja907982w

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Funding

  1. National Science Foundation
  2. Research Corporation for Science Advancement

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A copper-promoted coupling of vinyl pinacol boronate esters and alcohols for the synthesis of enol ethers is reported. The reaction occurs In 50-99% yield and is compatible with a variety of functional groups. Cupric acetate is the copper Source, and triethylamine buffer is used to prevent protodeboration; the reaction occurs at room temperature. In addition to excellent chemoselectivity, the reaction is stereospecific.

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