Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
J Am Chem Soc. 2009 Dec 23;131(50):18057-9. doi: 10.1021/ja906514s.
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 BF(3).OEt(2)-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.
在苛刻的碱性或酸性条件下通过 C-O 键形成醚是有机化学中一种根深蒂固的合成断裂方法。我们报告了一种替代方法，涉及 BF(3)。OEt(2)促进稳定、易于制备的缩醛与广泛可用的钾芳基、烯基和炔基三氟硼酸盐的偶联。这种快速、操作简单的过程提供了直接制备二烷基醚的途径，其中许多醚用经典方法难以制备。使用 MOM 保护的醇和缩醛保护的醛可以在不进行保护基操作或强碱的情况下形成醚。
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