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金属催化的卤代炔基化反应

Metal-Catalyzed Haloalkynylation Reactions.

作者信息

Kreuzahler Mathis, Haberhauer Gebhard

机构信息

Institut für Organische Chemie, Universität Duisburg-Essen, Universitätsstraße 7, 45117, Essen, Germany.

出版信息

Chemistry. 2022 Jan 19;28(4):e202103046. doi: 10.1002/chem.202103046. Epub 2021 Nov 18.

DOI:10.1002/chem.202103046
PMID:34644433
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9299716/
Abstract

Metal catalysis has revolutionized synthetic chemistry, leading to entirely new, very efficient transformations, which enable access to complex functionalized molecules. One such new transformation method is the haloalkynylation reaction, in which both a halogen atom and an alkynyl unit are transferred to an unsaturated carbon-carbon bond. This minireview summarizes the development of metal-catalyzed haloalkynylation reactions since their beginning about a decade ago. So far, arynes, alkenes and alkynes have been used as unsaturated systems and the reactivities of these systems are summarized in individual chapters of the minireview. Especially, the last few years have witnessed a rapid development due to gold-catalyzed reactions. Here, we discuss how the choice of the catalytic system influences the regio- and stereoselectivity of the addition.

摘要

金属催化彻底改变了合成化学,带来了全新且高效的转化反应,从而能够合成复杂的功能化分子。一种这样的新转化方法是卤代炔基化反应,其中卤素原子和炔基单元都被转移到不饱和碳 - 碳键上。这篇综述总结了自大约十年前金属催化的卤代炔基化反应开始以来的发展情况。到目前为止,芳炔、烯烃和炔烃已被用作不饱和体系,并且这些体系的反应活性在综述的各个章节中进行了总结。特别是,由于金催化反应,在过去几年中该反应得到了快速发展。在此,我们讨论催化体系的选择如何影响加成反应的区域选择性和立体选择性。

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Chem Rev. 2021 Feb 24;121(4):2413-2444. doi: 10.1021/acs.chemrev.0c00825. Epub 2021 Jan 25.
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6
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7
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