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

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 protodebo...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-02, Vol.132 (4), p.1202-1203
Main Authors: Shade, Ryan E, Hyde, Alan M, Olsen, John-Carl, Merlic, Craig A
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja907982w