508223-55-0Relevant academic research and scientific papers
Transition metal-free direct C–H trifluoromethyltion of (hetero)arenes with Togni's reagent
Chen, Xiaoyu,Ding, Licheng,Li, Linlin,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, (2019/12/30)
A new transition-metal-free direct C–H trifluoromethylation reaction of (hetero)arenes with Togni's reagent was developed. This transformation proceeded smoothly under mild conditions and exhibited good tolerance of many synthetically relevant functional groups. It provided an alternative approach for the synthesis of trifluoromethylated (hetero)arenes.
Preparation method of trifluoromethylated aniline compound
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Paragraph 0113-0121, (2020/12/30)
The invention provides a preparation method of a trifluoromethylated aniline compound shown in a formula (IIA) or a formula (IIB). The method comprises the following steps: by taking a mixed solvent of DMF and water in a volume ratio of 1:(1-4) as a reaction medium, adding an aniline compound shown in a formula (IA) or a formula (IB), 1-(trifluoromethyl)-1,2-benziodoxol-3-(1H)-one and a photocatalyst, and reacting for 2-6 hours at room temperature under blue light; and carrying out post-treatment on the obtained reaction mixture to obtain the trifluoromethylated aniline compound as shown in the formula (IIA) or the formula (IIB). According to the method, by the photocatalyst, the reaction is driven to be carried out under the irradiation of visible light, the reaction conditions are mild,the site selectivity is high, the reaction is efficient, green and environment-friendly, the reaction yield can reach 90%, and the product can be prepared by only one step.
Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation
Mihai, Madalina T.,Williams, Benjamin D.,Phipps, Robert J.
supporting information, p. 15477 - 15482 (2019/10/11)
The selective functionalization of C-H bonds at the arene para position is highly challenging using transition metal catalysis. Iridium-catalyzed borylation has emerged as a leading technique for arene functionalization, but there are only a handful of strategies for para-selective borylation, which operate on specific substrate classes and use bespoke ligands or catalysts. We describe a remarkably general protocol which results in para-selectivity on some of the most common arene building blocks (anilines, benzylamines, phenols, benzyl alcohols) and uses standard borylation ligands. Our strategy hinges upon the facile conversion of the substrates into sulfate or sulfamate salts, wherein the anionic arene component is paired with a tetrabutylammonium cation. We hypothesize that the bulk of this cation disfavors meta-C-H borylation, thereby promoting the challenging para-selective reaction.
Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni's Reagent
Gao, Xianying,Geng, Yang,Han, Shuaijun,Liang, Apeng,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie
supporting information, p. 3732 - 3735 (2018/07/22)
An efficient nickel-catalyzed C-H trifluoromethylation for the synthesis of trifluoromethylated free anilines using Togni's reagent has been developed. This approach exhibits a good functional group tolerance, good regioselectivity, and chemoselectivity under mild conditions. The newly developed economical one-step method is a better alternative to synthesize trifluoromethylated free anilines.
Preparation method of trifluoromethylamine
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Paragraph 0166-0170, (2018/09/28)
The invention relates to a preparation method of trifluoromethylamine. The method includes the following steps that aromatic amine shown in the formula (1) and a trifluoromethyl reagent shown in the formula (2) react in a solvent under the condition that an alkali and/or nickel compound exists, and the trifluoromethylamine compound shown in the formula (3) is generated. According to the preparation method of trifluoromethylamine, aromatic amine and 1-trifluoromethyl-1,2-iodobenzoyl-3(H)-ketone serve as raw materials and react under the condition that the alkali and/or nickel compound exists through the amino positioning effect on aromatic nucleus. The synthesis steps of the method are simple, the cost of the raw materials is low, the production cost of trifluoromethylamine can be greatly reduced, and large-scale industrialized production is promoted.
Visible-light-mediated direct perfluoroalkylation and trifluoromethylation of free anilines
He, Chun-Yang,Gu, Ji-Wei,Zhang, Xingang
supporting information, p. 3939 - 3941 (2017/09/21)
A mild, operationally simple method for direct perfluoroalkylation and trifluoromethylation of anilines through visible-light-mediated photoredox catalysis from broadly available perfluoroalkyl iodides and free anilines is described. The method provides a facile route for application in drug discovery and development.
3-(PYRIDIN-3-YL)-ACRYLAMIDE AND N-(PYRIDIN-3-YL)-ACRYLAMIDE DERIVATIVES AND THEIR USE AS PAK OR NAMPT MODULATORS
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Paragraph 00303, (2017/03/14)
The invention generally relates to cyclic compounds and, more particularly, to a compound represented by Structural Formula I: or a pharmaceutically acceptable salt thereof and pharmaceutical compositions comprising the multicyclic compounds. The invention also relates to a method for treating a disease or disorder selected from cancer (e.g., lymphoma, such as mantle cell lymphoma), a neurodegenerative disease, an inflammatory diseases or an immune system disease (e.g., a T- Cell mediated autoimmune diseases) in a subject in need thereof. The method comprises administering to a subject in need thereof a therapeutically effective amount of a compound of the invention, or a pharmaceutically acceptable salt thereof, or a composition comprising a compound of the invention, or a pharmaceutically acceptable salt thereof.
A for the preparation of ortho-trifluoromethyl-aniline or its derivatives (by machine translation)
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Paragraph 0031-0032, (2016/10/24)
The invention discloses a method for preparing o-trifluoromethyl phenylamine and derivatives thereof. According to the method, phenylamine or a phenylamine derivative serving as raw material reacts with a trivalent iodine reagent compound 2 in a solution under the protection of argon or nitrogen and illumination condition in the presence of tri(2-phenylpyridine)-iridium [Ir(ppy)3] serving as a catalyst to produce o-trifluorophenylamine or derivatives thereof 3, wherein the trivalent iodine reagent compound 2 has a structure shown in the specification. The method is mild in reaction conditions, the amino does not need to be protected, and trifluoromethyl substituted phenylamine or phenylamine derivatives can be directly obtained.
Visible-light-promoted radical C-H trifluoromethylation of free anilines
Xie, Jin,Yuan, Xiangai,Abdukader, Ablimit,Zhu, Chengjian,Ma, Jing
supporting information, p. 1768 - 1771 (2014/04/17)
The trifluoromethyl-substituted anilines are biologically active compounds and useful building blocks. In this communication, we have developed the first visible-light-induced radical trifluoromethylation of free anilines with the commercially available and easily handled Togni reagent at room temperature. The resulting products were successfully transformed into a variety of valuable fluorine-containing molecules and heterocyclic compounds. This protocol provides an economical and powerful route to trifluoromethylated free anilines.
PXPd-catalyzed borylation of aniline derivatives
Wheaton, Susan L.,Kabir, S.M. Humanayun,Zhang, Haiwen,Vogels, Christopher M.,Decken, Andreas,Westcott, Stephen A.
experimental part, p. 725 - 731 (2011/11/04)
Addition of pinacolborane (HBO2C2Me4) to 2-iodoaniline can be catalyzed using a number of palladium complexes, including [(t-Bu)2PCl]2PdCl2 (PXPd), to give the corresponding boronate ester 2-H2NC6H4(BO2C2Me4) in excellent yields. The PXPd system could also be used in the catalyzed borylation of substituted anilines to give the corresponding aminoboronate esters in moderate to high yields.
