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用于联芳基合成的脱羧氧化交叉偶联反应的最新进展

Recent Progress in Decarboxylative Oxidative Cross-Coupling for Biaryl Synthesis.

作者信息

Perry Gregory J P, Larrosa Igor

机构信息

School of Chemistry University of Manchester Oxford Road M13 9PL Manchester U.K.

出版信息

European J Org Chem. 2017 Jul 7;2017(25):3517-3527. doi: 10.1002/ejoc.201700121. Epub 2017 Apr 26.

DOI:10.1002/ejoc.201700121
PMID:29354019
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5763354/
Abstract

The beginning of the 21st century has seen tremendous growth in the field of decarboxylative activation. Benzoic acid derivatives are now recognised as atom-economic alternatives to traditional cross-coupling partners, and they also benefit from being inexpensive, readily available and shelf-stable reagents. In this microreview we discuss recent developments in the coupling of benzoic acid derivatives either with an arene or with a second benzoic acid derivative, a process often termed decarboxylative oxidative cross-coupling. These procedures offer great promise for the development of highly selective and atom-economic cross-couplings.

摘要

21世纪初，脱羧活化领域取得了巨大发展。如今，苯甲酸衍生物被认为是传统交叉偶联试剂的原子经济性替代品，它们还具有价格低廉、易于获得且储存稳定的优点。在这篇微型综述中，我们讨论了苯甲酸衍生物与芳烃或与另一种苯甲酸衍生物偶联的最新进展，这一过程通常称为脱羧氧化交叉偶联。这些方法为开发高选择性和原子经济性的交叉偶联反应带来了巨大希望。

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2
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Chem Commun (Camb). 2015 Oct 18;51(81):15059-62. doi: 10.1039/c5cc06645j.
3
Copper-/Silver-Mediated Arylation of C(sp(2))-H Bonds with 2-Thiophenecarboxylic Acids.铜/银介导的 2-噻吩甲酸 C(sp(2))-H 芳基化反应。
通过定向Heck-脱羧偶联反应，二烯二酸作为一种有用的二烯结构单元。
Commun Chem. 2020 Apr 20;3(1):48. doi: 10.1038/s42004-020-0295-0.
4
Decarboxylative cross-coupling reactions for P(O)-C bond formation.用于形成P（O）-C键的脱羧交叉偶联反应。
RSC Adv. 2018 Jul 24;8(46):26383-26398. doi: 10.1039/c8ra04557g. eCollection 2018 Jul 19.
5
Recent developments in decarboxylative cross-coupling reactions between carboxylic acids and N-H compounds.羧酸与N-H化合物之间脱羧交叉偶联反应的最新进展。
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6
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4
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9
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10
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J Am Chem Soc. 2014 Mar 19;136(11):4109-12. doi: 10.1021/ja500457s. Epub 2014 Mar 11.