Chemoselective Suzuki-Miyaura Cross-Coupling via Kinetic Transmetallation
Chemoselective Suzuki-Miyaura Cross-Coupling via Kinetic Transmetallation
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DOI：
10.1002/anie.201610797
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发表时间：
2017-01-24
影响因子：
16.6
通讯作者：
Watson, Allan J. B.
中科院分区：
文献类型：
--
作者：
Fyfe, James W. B.;Fazakerley, Neal J.;Watson, Allan J. B.
化学选择性Suzuki-Miyaura交叉偶联通常需要一种亲核试剂对transmetabolites的设计失活。在这里，我们表明，硼酸可以化学选择性反应的存在下，表面上等效的反应硼酸频哪醇（BPin）酯的动力学歧视transmetabolism。同时亲电控制允许在不存在保护基团的情况下在单个操作中进行顺序的化学选择性交叉偶联。
Chemoselective Suzuki-Miyaura cross-coupling generally requires a designed deactivation of one nucleophile towards transmetallation. Here we show that boronic acids can be chemoselectively reacted in the presence of ostensibly equivalently reactive boronic acid pinacol (BPin) esters by kinetic discrimination during transmetallation. Simultaneous electrophile control allows sequential chemoselective crosscouplings in a single operation in the absence of protecting groups.