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稳定货架的亲电三氟甲基化试剂:简要历史透视。

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective.

机构信息

Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

出版信息

Beilstein J Org Chem. 2010 Jun 16;6:65. doi: 10.3762/bjoc.6.65.

DOI:10.3762/bjoc.6.65
PMID:20703379
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2919266/
Abstract

Since the discovery by Yagupolskii and co-workers that S-trifluoromethyl diarylsulfonium salts are effective for the trifluoromethylation of thiophenolates, the design and synthesis of electrophilic trifluoromethylating reagents have been extensively researched in both academia and industry, due to the significant unique features that trifluoromethylated compounds have in pharmaceuticals, agricultural chemicals, and functional materials. Several effective reagents have been developed by the groups of Yagupolskii, Umemoto, Shreeve, Adachi, Magnier, Togni and Shibata. Due to the high stability and reactivity of these reagents, a series of Umemoto reagents, Togni reagent and Shibata reagent are now commercially available. In this review, we wish to briefly provide a historical perspective of the development of so-called "shelf-stable electrophilic trifluoromethylating reagents", although this field is in constant development.

摘要

自 Yagupolskii 及其同事发现 S-三氟甲基二芳基锍盐可有效用于硫酚盐的三氟甲基化以来,由于三氟甲基化化合物在药物、农药和功能材料中具有显著的独特性质,学术界和工业界都在广泛研究设计和合成亲电三氟甲基化试剂。Yagupolskii、Umemoto、Shreeve、Adachi、Magnier、Togni 和 Shibata 等小组已经开发出了几种有效的试剂。由于这些试剂具有高稳定性和反应活性,一系列 Umemoto 试剂、Togni 试剂和 Shibata 试剂现已商品化。在本文综述中,我们希望简要介绍一下所谓的“稳定的亲电三氟甲基化试剂”的发展历史,尽管该领域还在不断发展。

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Chem Commun (Camb). 2009 Oct 28(40):5993-5. doi: 10.1039/b913962a. Epub 2009 Sep 14.
5
Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.通过光氧化还原有机催化实现醛的对映选择性α-三氟甲基化反应。
J Am Chem Soc. 2009 Aug 12;131(31):10875-7. doi: 10.1021/ja9053338.
6
Enantioselective electrophilic trifluoromethylation of beta-keto esters with Umemoto reagents induced by chiral nonracemic guanidines.由手性非外消旋胍引发的、使用梅本试剂对β-酮酯进行对映选择性亲电三氟甲基化反应。
Org Biomol Chem. 2009 Sep 7;7(17):3599-604. doi: 10.1039/b909641h. Epub 2009 Jul 10.
7
Zinc-mediated formation of trifluoromethyl ethers from alcohols and hypervalent iodine trifluoromethylation reagents.锌介导的由醇类和高价碘三氟甲基化试剂形成三氟甲基醚的反应。
Angew Chem Int Ed Engl. 2009;48(24):4332-6. doi: 10.1002/anie.200900974.
8
Update 1 of: Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.《不对称氟化、三氟甲基化及全氟烷基化反应》更新1
Chem Rev. 2008 Sep;108(9):PR1-43. doi: 10.1021/cr800221v.
9
Reactivity of a 10-I-3 hypervalent iodine trifluoromethylation reagent with phenols.一种10-I-3高价碘三氟甲基化试剂与酚类的反应活性。
J Org Chem. 2008 Oct 3;73(19):7678-85. doi: 10.1021/jo8014825. Epub 2008 Sep 5.
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Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(iii)-CF(3) reagents.使用高价碘(III)-CF(3)试剂对仲芳基膦和伯芳基膦以及仲烷基膦和伯烷基膦进行温和的亲电三氟甲基化反应。
Chem Commun (Camb). 2008 Apr 7(13):1575-7. doi: 10.1039/b801424h. Epub 2008 Mar 3.