Synthesis of dialkyl ethers from organotrifluoroborates and acetals

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作者：
Mitchell, T. Andrew [1 ]
Bode, Jeffrey W. [1 ]
机构：
[1] Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, United States
来源：
Journal of the American Chemical Society | 2009年 / 131卷 / 50期
关键词：
(Chemical Equation Presented) The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF3•OEt2-promoted coupling of stable; easily prepared acetals with widely available potassium aryl-; alkenyl-; and alkynyltrifluoroborates. This fast; operationally simple process offers straightforward access to dialkyl ethers; many of which would be difficult to prepare using classical methods. The use of MOM-protected alcohols and acetal-protected aldehydes enables ether formation without recourse to protecting-group manipulations or strong bases. © 2009 American Chemical Society;
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页码：18057 / 18059
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