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芳基卤化物钯催化氰化反应的最新进展与前景

Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides.

作者信息

Neetha Mohan, Afsina C M A, Aneeja Thaipparambil, Anilkumar Gopinathan

机构信息

School of Chemical Sciences, Mahatma Gandhi University Priyadarsini Hills P. O. Kottayam Kerala India 686560

Advanced Molecular Materials Research Centre (AMMRC), Mahatma Gandhi University Priyadarsini Hills P. O. Kottayam Kerala India 686560.

出版信息

RSC Adv. 2020 Sep 11;10(56):33683-33699. doi: 10.1039/d0ra05960a. eCollection 2020 Sep 10.

DOI:10.1039/d0ra05960a
PMID:35519018
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9056778/
Abstract

Aryl nitriles are compounds with wide significance. They have made their own space in various sectors including pharmaceuticals, industries, natural product chemistry, and so on. Furthermore, they are also key intermediates in various transformations in organic chemistry. Transition metal-catalyzed cyanation reactions have proved to be a better replacement for the existing traditional synthetic strategies for aryl nitriles. Palladium is one of the most studied transition metals other than copper and nickel owing to its wide functional group compatibility and catalytic efficacy. There have been drastic developments in the field of palladium-catalyzed cyanation since its discovery in the 1973. This review summarizes the recent developments in the palladium-catalyzed cyanation of aryl halides and covers literature from 2012-2020.

摘要

芳基腈是具有广泛重要性的化合物。它们在包括制药、工业、天然产物化学等在内的各个领域都占有一席之地。此外，它们也是有机化学中各种转化反应的关键中间体。过渡金属催化的氰化反应已被证明是现有传统芳基腈合成策略的更好替代方法。钯是除铜和镍之外研究最多的过渡金属之一，因其具有广泛的官能团兼容性和催化效率。自1973年发现以来，钯催化氰化领域取得了巨大进展。本综述总结了芳基卤化物钯催化氰化的最新进展，并涵盖了2012年至2020年的文献。

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Mater Sci Eng C Mater Biol Appl. 2019 Nov;104:109919. doi: 10.1016/j.msec.2019.109919. Epub 2019 Jun 26.
4
Pd Nanocatalyst Adorning Coral Reef Nanocomposite for the Synthesis of Nitriles: Utility of Leaf Extract as a Stabilizing and Reducing Agent.用于合成腈的负载钯纳米催化剂的珊瑚礁纳米复合材料：叶提取物作为稳定剂和还原剂的效用
Nanomaterials (Basel). 2019 Apr 7;9(4):565. doi: 10.3390/nano9040565.
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Palladium-Catalysed Synthesis and Transformation of Quinolones.钯催化喹诺酮类化合物的合成与转化。
Molecules. 2019 Jan 9;24(2):228. doi: 10.3390/molecules24020228.
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Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN).镍催化未活化的氯代或溴代烷基与氰化锌的氰化反应
Org Lett. 2018 Dec 7;20(23):7735-7739. doi: 10.1021/acs.orglett.8b03539. Epub 2018 Nov 15.
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Non-toxic cyanide sources and cyanating agents.无毒氰源和氰化剂。
Org Biomol Chem. 2018 Dec 19;17(1):11-23. doi: 10.1039/c8ob02140f.
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Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr/NIXANTPHOS-based Catalyst.氮杂芳基甲胺与芳基氯及基于NiBr/NIXANTPHOS的催化剂的芳基化反应
Adv Synth Catal. 2017 Aug 17;359(16):2890-2894. doi: 10.1002/adsc.201700438. Epub 2017 Jul 12.
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Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review.钯金属催化剂在 21 世纪的交叉偶联反应及相关反应中的应用：批判性回顾。
Chem Rev. 2018 Feb 28;118(4):2249-2295. doi: 10.1021/acs.chemrev.7b00443. Epub 2018 Feb 20.
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Palladium-Catalyzed Safe Cyanation of Aryl Iodides with Hexamethylenetetramine.钯催化六亚甲基四胺对芳基碘的安全氰化反应。
J Org Chem. 2017 Dec 1;82(23):12888-12891. doi: 10.1021/acs.joc.7b02373. Epub 2017 Nov 15.