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钴(III)催化的三组分 C-H 键加成反应实现官能化烯基卤化物的汇聚合成。

A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C-H Bond Addition.

机构信息

Department of Chemistry, Yale University, 225 Prospect St., New Haven, CT, 06520, USA.

出版信息

Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9976-9980. doi: 10.1002/anie.201705817. Epub 2017 Jul 17.

DOI:10.1002/anie.201705817
PMID:28657674
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5568819/
Abstract

A Co -catalyzed three-component coupling of C(sp )-H bonds, alkynes, and halogenating agents to give alkenyl halides is reported. This transformation proceeds with high regio- and diastereoselectivity, and is effective for a broad range of aryl and alkyl terminal alkynes. Diverse C-H bond partners also exhibit good reactivity for a range of heteroaryl and aryl systems as well as synthetically useful secondary and tertiary amide, urea, and pyrazole directing groups. This multicomponent transformation is also compatible with allenes in place of alkynes to furnish tetrasubstituted alkenyl halides, showcasing the first halo-arylation of allenes.

摘要

本文报道了一种 C(sp )-H 键、炔烃和卤化试剂的协同三组分偶联反应，生成烯基卤化物。该转化具有高区域和立体选择性，对广泛的芳基和烷基末端炔烃有效。各种 C-H 键供体对各种杂芳基和芳基体系以及合成上有用的仲和叔酰胺、脲和吡唑导向基团也表现出良好的反应性。该多组分转化也与丙二烯兼容，以提供四取代的烯基卤化物，展示了丙二烯的首例卤芳基化反应。

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