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铁催化有机锂化合物与有机卤化物的交叉偶联反应。

Iron-catalysed cross-coupling of organolithium compounds with organic halides.

作者信息

Jia Zhenhua, Liu Qiang, Peng Xiao-Shui, Wong Henry N C

机构信息

Department of Chemistry, State Key Laboratory of Synthetic Chemistry and Centre of Novel Functional Molecules, Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.

Shenzhen Center of Novel Functional Molecules and Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, Shenzhen Research Institute, Chinese University of Hong Kong, No.10, Second Yuexing Road, Shenzhen 518507, China.

出版信息

Nat Commun. 2016 Feb 5;7:10614. doi: 10.1038/ncomms10614.

DOI:10.1038/ncomms10614
PMID:26847602
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4748252/
Abstract

In past decades, catalytic cross-coupling reactions between organic halides and organometallic reagents to construct carbon-carbon bond have achieved a tremendous progress. However, organolithium reagents have rarely been used in cross-coupling reactions, due mainly to their high reactivity. Another limitation of this transformation using organolithium reagents is how to control reactivity with excellent selectivity. Although palladium catalysis has been applied in this field recently, the development of an approach to replace catalytic systems of noble metals with nonprecious metals is currently in high demand. Herein, we report an efficient synthetic protocol involving iron-catalysed cross-coupling reactions employing organolithium compounds as key coupling partners to unite aryl, alkyl and benzyl fragments and also disclose an efficient iron-catalysed release-capture ethylene coupling with isopropyllithium.

摘要

在过去几十年中,有机卤化物与有机金属试剂之间用于构建碳-碳键的催化交叉偶联反应取得了巨大进展。然而,有机锂试剂很少用于交叉偶联反应,主要是因为它们的高反应活性。使用有机锂试剂进行这种转化的另一个限制是如何以优异的选择性控制反应活性。尽管钯催化最近已应用于该领域,但目前迫切需要开发一种用非贵金属取代贵金属催化体系的方法。在此,我们报告了一种高效的合成方案,该方案涉及铁催化的交叉偶联反应,使用有机锂化合物作为关键偶联伙伴来连接芳基、烷基和苄基片段,并且还公开了一种与异丙基锂进行的高效铁催化的释放-捕获乙烯偶联反应。

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