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

Ryan E. Shade, Alan M. Hyde, John-Carl Olsen and Craig A. Merlic*

*Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, Email: merlicchem.ucla.edu

R. E. Shade, A. M. Hyde, J.-C. Olsen, C. A. Merlic, J. Am. Chem. Soc., 2010, 132, 1202-1203.

DOI: 10.1021/ja907982w (free Supporting Information)


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Abstract

A stereospecific and stereoselective, copper-promoted coupling of vinyl pinacol boronate esters and alcohols allows the synthesis of enol ethers in very good yields, is compatible with various functional groups, and occurs at room temperature. Cupric acetate is the copper source, and triethylamine buffer is used to prevent protodeboration.

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Key Words

Chan-Lam Coupling, Ethers


ID: J48-Y2010-0270