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脱羧氟化策略在获得具有医学相关性产品中的应用。

Decarboxylative fluorination strategies for accessing medicinally- relevant products.

机构信息

Department of Medicinal Chemistry, the University of Kansas, 1251 Wescoe Hall Dr., 4046A Malott Hall, Lawrence, KS 66045, USA.

出版信息

Curr Top Med Chem. 2014;14(7):966-78. doi: 10.2174/1568026614666140202210850.

Abstract

Fluorinated organic compounds have a long history in medicinal chemistry, and synthetic methods to access target fluorinated compounds are undergoing a revolution. One powerful strategy for the installation of fluorinecontaining functional groups includes decarboxylative reactions. Benefits of decarboxylative approaches potentially include: 1) readily available substrates or reagents 2) mild reaction conditions; 3) simplified purification. This focus review highlights the applications of decarboxylation strategies for fluorination reactions to access compounds with biomedical potential. The manuscript highlights on two general strategies, fluorination by decarboxylative reagents and by decarboxylation of substrates. Where relevant, examples of medicinally useful compounds that can be accessed using these strategies are highlighted.

摘要

含氟有机化合物在药物化学中有悠久的历史,将目标含氟化合物合成的方法正在经历一场革命。一种用于引入含氟官能团的有力策略包括脱羧反应。脱羧方法的优点可能包括:1)易于获得的底物或试剂;2)温和的反应条件;3)简化的纯化。本综述重点介绍了脱羧策略在氟代反应中的应用,以获得具有生物医学潜力的化合物。本文强调了两种一般策略,即用脱羧试剂进行氟代和用底物进行脱羧。在相关的情况下,突出了可以使用这些策略获得的具有药用价值的化合物的实例。

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本文引用的文献

1
Radiosyntheses using fluorine-18: the art and science of late stage fluorination.
Curr Top Med Chem. 2014;14(7):875-900. doi: 10.2174/1568026614666140202205035.
2
Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis.
Chem Commun (Camb). 2014 Mar 4;50(18):2308-10. doi: 10.1039/c3cc48598f. Epub 2014 Jan 21.
3
Flow microreactor synthesis in organo-fluorine chemistry.
Beilstein J Org Chem. 2013 Dec 5;9:2793-802. doi: 10.3762/bjoc.9.314.
4
A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging.
Nat Chem. 2013 Nov;5(11):941-4. doi: 10.1038/nchem.1756. Epub 2013 Sep 8.
5
Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates.
Org Lett. 2013 Nov 1;15(21):5578-81. doi: 10.1021/ol402780k. Epub 2013 Oct 11.
6
Conversion between difluorocarbene and difluoromethylene ylide.
Chemistry. 2013 Nov 4;19(45):15261-6. doi: 10.1002/chem.201303248. Epub 2013 Sep 20.
7
S-, N-, and Se-difluoromethylation using sodium chlorodifluoroacetate.
Org Lett. 2013 Oct 4;15(19):5036-9. doi: 10.1021/ol402370f. Epub 2013 Sep 23.
8
Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system.
Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11628-31. doi: 10.1002/anie.201306094. Epub 2013 Sep 5.
9
Introduction of fluorine and fluorine-containing functional groups.
Angew Chem Int Ed Engl. 2013 Aug 5;52(32):8214-64. doi: 10.1002/anie.201206566. Epub 2013 Jul 19.
10
Synthesis and decarboxylative Wittig reaction of difluoromethylene phosphobetaine.
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