Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers

RE Shade, AM Hyde, JC Olsen…

Index: Shade, Ryan E.; Hyde, Alan M.; Olsen, John-Carl; Merlic, Craig A. Journal of the American Chemical Society, 2010 , vol. 132, p. 1202 - 1203

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Citation Number: 75

Abstract

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.