80959-78-0Relevant articles and documents
Exploring the Structure and Performance of Cd–Chalcogenide Photocatalysts in Selective Trifluoromethylation
Muralirajan, Krishnamoorthy,Kancherla, Rajesh,Bau, Jeremy A.,Taksande, Mayur Rahul,Qureshi, Muhammad,Takanabe, Kazuhiro,Rueping, Magnus
, p. 14772 - 14780 (2021/12/09)
The field of heterogeneous photoredox catalysis has grown substantially and impacted organic synthesis because of the affordability and reusability of catalysts. This study reports radical trifluoromethylation with Cd–chalcogenide semiconductors. Cd semiconductors, particularly CdSe, are readily available, commercial, visible-light-responsive, heterogeneous photocatalysts. The potential of readily available Cd semiconductors, particularly CdSe, is confirmed by their increased photocatalytic activity toward trifluoromethylation with various substrates, such as (hetero)arenes and vinylic amides/acids, via addition, cyclization, and decarboxylation under visible light. The economic significance of this strategy is also highlighted through the scalable synthesis of biologically active molecules followed by catalyst reuse. Moreover, these catalysts are relatively inexpensive compared with transition metal-based homogeneous photocatalysts, presently used in organic synthesis.
Rapid Syntheses of [11C]Arylvinyltrifluoromethanes through Treatment of (E)-Arylvinyl(phenyl)iodonium Tosylates with [11C]Trifluoromethylcopper(I)
Jana, Susovan,Telu, Sanjay,Yang, Bo Yeun,Haskali, Mohammad B.,Jakobsson, Jimmy E.,Pike, Victor W.
supporting information, p. 4574 - 4578 (2020/06/05)
We report a method for labeling arylvinyltrifluoromethanes with carbon-11 (t1/2 = 20.4 min) as representatives of a new radiolabeled chemotype that has potential for developing radiotracers for biomedical imaging with positron emission tomography. Treatme
Electrochemical Synthesis Strategy for Cvinyl-CF3 Compounds through Decarboxylative Trifluoromethylation
Hong, Huanliang,Li, Yibiao,Chen, Lu,Li, Bin,Zhu, Zhongzhi,Chen, Xiuwen,Chen, Ling,Huang, Yubing
, p. 5980 - 5986 (2019/05/10)
An efficient decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids using the Langlois reagent as a trifluoromethyl precursor has been achieved by an electro-oxidative strategy. Under catalyst-free and external oxidant-free electrolysis
Merging hypervalent iodine and sulfoximine chemistry: A new electrophilic trifluoromethylation reagent
Kalim, Jorna,Duhail, Thibaut,Le, Thanh-Nghi,Vanthuyne, Nicolas,Anselmi, Elsa,Togni, Antonio,Magnier, Emmanuel
, p. 10516 - 10523 (2019/12/02)
Electrophilic trifluoromethylation is at the forefront of methodologies available for the installation of the CF3 moiety to organic molecules; research in this field is largely spurred by the availability of stable and accessible trifluoromethy
Electrochemical Decarboxylative Trifluoromethylation of α, β-Unsaturated Carboxylic Acids with CF3SO2Na
Li, Fang-Yuan,Lin, Dian-Zhao,He, Tian-Jun,Zhong, Wei-Qiang,Huang, Jing-Mei
, p. 2350 - 2354 (2019/04/13)
A new method for the synthesis of vinyl trifluoromethyl compounds from α, β-unsaturated carboxylic acids and CF3SO2Na has been developed. This electrochemical decarboxylative trifluoro-methylation was found to be highly stereoselective and afforded products in good yields with wide substrate scope under metal-free and external chemical oxidant-free conditions.
Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents
Wang, Minyan,Pu, Xinghui,Zhao, Yunfei,Wang, Panpan,Li, Zexian,Zhu, Chendan,Shi, Zhuangzhi
supporting information, p. 9061 - 9065 (2018/08/03)
A copper-catalyzed system has been introduced for the enantioselective defluoroalkylation of linear 1-(trifluoromethyl)alkenes through C-F activation to synthesize various gem-difluoroalkenes as carbonyl mimics. For the first time, arylboronate-activated alkyl Grignard reagents were uncovered in this cross-coupling reaction. Mechanistic studies confirmed that the tetraorganoborate complexes generated in situ were the key reactive species for this transformation.
Method for synthesizing olefin compound by photo-induced one-pot process
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Paragraph 0093-0095, (2018/11/03)
The invention discloses a method for synthesizing an olefin compound by a photo-induced one-pot process. The method comprises the following step of subjecting a halohydrocarbon and an aldehyde compound to a reaction under the condition of irradiation in an inert atmosphere by taking alkali metal carbonate as a base, taking an organic phosphine compound as an adjuvant and taking a photosensitizer as a catalyst, thereby obtaining the olefin compound. According to the method disclosed by the invention, the olefin compound is produced from the halohydrocarbon and the aldehyde compound in a high-yield manner under the condition of irradiation in the inert atmosphere under normal-temperature reaction conditions by taking acetonitrile, DMF (N,N-dimethylformamide) or DMA (N,N-dimethylacetamide) asa solvent, taking an organic phosphine reagent as a reaction adjuvant, taking the alkali metal carbonate as the base and taking the photosensitizer as the catalyst. Compared with the conventional olefin synthesis methods, the method disclosed by the invention has the obvious advantages that the reaction raw materials are readily available, the tolerance to a variety of functional groups on halohydrocarbons and aldehydes is high, the yield is high, the separation and purification of a product are simple and convenient, and the like.
Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF3]
He, Lisi,Yang, Xinkan,Tsui, Gavin Chit
, p. 6192 - 6201 (2017/06/23)
A domino hydroboration/trifluoromethylation (formal hydrotrifluoromethylation) of alkynes using the fluoroform-derived [CuCF3] reagent is achieved. Synthetically useful (E)-alkenyl-CF3 building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes. The ultimate source of CF3 is the inexpensive industrial waste fluoroform.
Metal-free radical trifluoromethylation of β-nitroalkenes through visible-light photoredox catalysis
Midya, Siba P.,Rana, Jagannath,Abraham, Thomas,Aswin, Bhaskaran,Balaraman, Ekambaram
, p. 6760 - 6763 (2017/07/10)
A catalytic method for functional group interconversion is immensely important in modern sciences. Here, we report an efficient catalytic conversion of nitroalkenes to highly stereoselective 1-trifluoromethylalkenes at room temperature. This unprecedented metal-free photocatalytic strategy is simple and operates under visible-light irradiation using the commercially available CF3 source.
Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: An efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives
Zhao, Yilong,Zhou, Yuhan,Zhang, Chunxia,Wang, Huan,Zhao, Jinfeng,Jin, Kun,Liu, Jihong,Liu, Jianhui,Qu, Jingping
, p. 5693 - 5700 (2017/07/22)
A Pd-catalyzed hydrogenation of (Z)-trifluoromethyl alkenyl triflate providing either (Z)- or (E)-3,3,3-trifluoropropenyl derivatives with excellent divergent geometric control in good yield is described. Catalyzed by Pd(OAc)2/PPh3, the reduction of (Z)-trifluoromethyl alkenyl triflates with HSiEt3 gave (E)-3,3,3-trifluoropropenyl derivatives, and while using HCOOH/Et3N as the reducing agent, the (Z)-isomers were obtained through an elimination/hydrogenation tandem pathway. Both transformations showed excellent geometrical selectivity.
