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过渡金属催化的烯烃1,2-碳硼化反应:策略、机理及立体化学控制

Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

作者信息

Liu Zhen, Gao Yang, Zeng Tian, Engle Keary M

机构信息

Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92307 (USA).

Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA).

出版信息

Isr J Chem. 2020 Mar;60(3-4):219-229. doi: 10.1002/ijch.201900087. Epub 2019 Sep 10.

DOI:10.1002/ijch.201900087
PMID:33785969
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8006804/
Abstract

During the past decade, many research groups have described catalytic methods for 1,2-carboboration, allowing access to structurally complex organoboronates from alkenes. Various transition metals, especially copper, palladium, and nickel, have been widely used in these reactions. This review summarizes advances in this field, with a special focus on the catalytic cycles involved in different metal-catalyzed carboboration reactions, as well as the regio- and stereochemical consequences of the underlying mechanisms. 1,2-Carboboration of other unsaturated systems, such as alkynes and allenes, are outside of the scope of this review.

摘要

在过去十年中,许多研究小组都描述了1,2-碳硼化的催化方法,使得从烯烃出发能够获得结构复杂的有机硼酸酯。各种过渡金属,尤其是铜、钯和镍,已被广泛应用于这些反应中。本综述总结了该领域的进展,特别关注不同金属催化的碳硼化反应中涉及的催化循环,以及潜在机理的区域和立体化学结果。其他不饱和体系(如炔烃和联烯)的1,2-碳硼化不在本综述范围内。

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2
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3
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4
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5
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J Am Chem Soc. 2022 Oct 19;144(41):19173-19185. doi: 10.1021/jacs.2c08803. Epub 2022 Oct 5.
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J Am Chem Soc. 2019 Aug 14;141(32):12770-12779. doi: 10.1021/jacs.9b05583. Epub 2019 Aug 2.
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5
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7
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8
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Angew Chem Int Ed Engl. 2019 Mar 26;58(14):4612-4616. doi: 10.1002/anie.201814572. Epub 2019 Mar 3.