催化剂控制的二烯芳烃区域选择性硼化反应。
Catalyst Controlled Regiodivergent Arylboration of Dienes.
机构信息
Department of Chemistry, Indiana University , 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, United States.
出版信息
J Am Chem Soc. 2017 Jul 26;139(29):9823-9826. doi: 10.1021/jacs.7b05477. Epub 2017 Jul 12.
Abstract
A method for the regiodivergent arylboration of dienes is presented. These reactions allow for the formation of a diverse range of synthetically versatile products from simple precursors. Through mechanistic studies, these reactions likely operate by initial addition of a Cu-Bpin complex across the diene followed by Pd-catalyzed cross coupling with an aryl halide or pseudohalide.
摘要
本文提出了一种区域发散的二烯芳基化方法。这些反应可以从简单的前体中形成多种多样的合成多功能产物。通过机理研究，这些反应可能是通过 Cu-Bpin 配合物初始加成到二烯上，然后再与芳基卤化物或拟卤化物进行 Pd 催化交叉偶联来进行的。
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2
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