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通过镍氢催化含硼烯烃的远程氢芳基化快速合成高官能化烷基硼酸酯

Rapid Access to Highly Functionalized Alkyl Boronates by NiH-Catalyzed Remote Hydroarylation of Boron-Containing Alkenes.

作者信息

Zhang Yao, Han Bo, Zhu Shaolin

机构信息

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.

出版信息

Angew Chem Int Ed Engl. 2019 Sep 23;58(39):13860-13864. doi: 10.1002/anie.201907185. Epub 2019 Jul 26.

DOI:10.1002/anie.201907185
PMID:31287597
Abstract

The direct and selective functionalization of relatively simple and readily accessible precursors to produce highly functionalized alkyl boronates is a synthetically useful process. Herein we report a NiH-catalyzed remote hydroarylation process that can, through a synergistic combination of chain walking and subsequent cross-coupling, introduce an aryl group at the adjacent carbon atom of alkyl boronates under mild conditions. By means of a preliminary experiment with moderate enantioselectivity, it was shown that an asymmetric version could also be realized.

摘要

将相对简单且易于获得的前体直接进行选择性官能团化以制备高度官能团化的硼酸烷基酯是一种具有合成价值的过程。在此,我们报道了一种NiH催化的远程氢芳基化过程,该过程可以通过链行走和随后的交叉偶联的协同组合,在温和条件下将芳基引入硼酸烷基酯的相邻碳原子上。通过具有适度对映选择性的初步实验表明,也可以实现不对称版本。

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