镍催化的色烯缩醛与硼酸的交叉偶联反应。
Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.
机构信息
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
出版信息
Org Lett. 2012 Mar 16;14(6):1616-9. doi: 10.1021/ol300364s. Epub 2012 Mar 2.
Abstract
A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo C(sp(3))-O activation and C(sp(3))-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin methyl ester.
摘要
描述了一种用于合成 2-芳基和杂芳基-2H-色烯的模块化、高效的方法。在无碱条件下，易得的 2-乙氧基-2H-色烯在廉价镍催化剂和硼酸的存在下经历 C(sp(3))-O 活化和 C(sp(3))-C 键形成。这种新策略可以广泛获得 2-取代的 2H-色烯，并已应用于包括洛他定和吲哚美辛甲酯在内的复杂分子的后期引入。
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