659-21-2Relevant articles and documents
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
Iron(III) Porphyrin Catalyzed Olefination of Aldehydes with 2,2,2-Trifluorodiazoethane (CF3CHN2)
Lu, Yang,Huang, Chuyu,Liu, Chao,Guo, Yong,Chen, Qing-Yun
, p. 2082 - 2090 (2018/05/31)
An efficient method for the iron(III) porphyrin catalyzed olefination of various aldehydes with 2,2,2-trifluorodiazoethane under neutral conditions is described. This transformation was shown to have a broad substrate scope and provide the corresponding CF3-substituted alkenes in good yields. The number of equivalents of PPh3 that is used in this reaction is crucial to the success of the olefination process. This reaction is a useful supplement to the synthetic applications of CF3CHN2.
Metal-free alkene oxy- and amino-perfluoroalkylations: Via carbocation formation by using perfluoro acid anhydrides: Unique reactivity between styrenes and perfluoro diacyl peroxides
Valverde, Elena,Kawamura, Shintaro,Sekine, Daisuke,Sodeoka, Mikiko
, p. 7115 - 7121 (2018/09/25)
We present a strategy for metal-free, alkene difunctionalization-type, oxy- and amino-perfluoroalkylations, using perfluoro acid anhydrides as practical and user-friendly perfluoroalkyl sources. This method provides efficient access to oxy-perfluoroalkylation products via carbocation formation due to the unique reactivity between styrenes and bis(perfluoroacyl) peroxides generated in situ from perfluoro acid anhydrides. This reaction is also applicable to metal-free intramolecular amino-perfluoroalkylation of styrenes bearing a pendant amino group. Synthetic utility of the oxy-trifluoromethylation products was confirmed by demonstrating derivatization via hydrolysis, elimination, and acid-catalyzed substitution with carbon nucleophiles. The mechanism of the carbocation formation was investigated experimentally and theoretically.
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.
Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of Cvinyl-CF3 Compounds with Togni (II) Reagent
Ma, Jing-Jing,Yi, Wen-Bin,Lu, Guo-Ping,Cai, Chun
supporting information, p. 3447 - 3452 (2016/01/25)
A highly efficient dimethylformamide (DMF)-promoted decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with Togni (II) reagent under metal-free conditions has been developed. The reactions showed good yields, high stereoselectivities and excellent functional group tolerance. Mechanistic studies confirmed that free-radical processes were involved in this system since the CF3 radical had been clearly trapped by scavengers. This method has been extended to the denitrative trifluoromethylation of β-nitrostyrenes in the presence of an iron(III) catalyst.
Facile synthesis of 1-trifluoromethylalkenes via the decarboxylation of α-trifluoromethyl-β-lactones
Veeraraghavan Ramachandran,Otoo, Barnabas
, p. 12388 - 12390 (2015/08/03)
DCC-mediated cyclodehydration of α-trifluoromethyl-β-hydroxy acids provides α-trifluoromethylated β-lactone intermediates, without loss of stereoselectivity. These lactones undergo facile decarboxylation providing a simple route to obtain both alkyl and aryl trifluoromethylated alkenes in excellent yields and stereoselectivity.
Sunlight-driven trifluoromethylation of olefinic substrates by photoredox catalysis: A green organic process
Akita, Munetaka,Koike, Takashi
, p. 742 - 751 (2015/07/15)
The principles and utility of photoredox catalysis in organic synthesis are described. After a brief description of the features of the two types of catalytic photoredox processes following the reductive quenching cycle (RQC) and the oxidative quenching cycle (OQC), the discussion is focused on organic transformations based on OQC, in particular the trifluoromethylation of olefinic substrates with electrophilic trifluoromethylating reagents furnishing solvolytic addition products and substitution products. It is concluded that catalytic photoredox systems are green from the point of view of harmfulness, safety, and energy source (visible light, including sunlight). Future prospects of photoredox catalysis will be also discussed.
Palladium catalyzed vinyltrifluoromethylation of aryl halides through decarboxylative cross-coupling with 2-(trifluoromethyl)acrylic acid
Kathiravan, Subban,Nicholls, Ian A.
supporting information, p. 1874 - 1877 (2015/04/27)
An efficient Pd-catalyzed stereoselective vinyltrifluoromethylation of aryl halides, through decarboxylative cross-coupling with 2-(trifluoromethyl)acrylic acid is described. The ready availability of the starting materials, the high level of functional group tolerance, and excellent E/Z selectivity make this protocol a safe and operationally convenient strategy for efficient synthesis of vinyltrifluoromethyl derivatives.
Controlled trifluoromethylation reactions of alkynes through visible-light photoredox catalysis
Iqbal, Naeem,Jung, Jaehun,Park, Sehyun,Cho, Eun Jin
supporting information, p. 539 - 542 (2014/01/23)
The control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3-containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF 3I by environmentally benign and efficient visible-light photoredox catalysis. Subtle differences in the combination of catalyst, base, and solvent enabled the control of reactivity and selectivity for the reaction between an alkyne and CF3I. Variety through selectivity: Highly valuable trifluoromethylated alkenyl iodides, alkenes, and alkynes were selectively generated from alkynes and CF3I by environmentally benign and efficient visible-light photoredox catalysis. A suitable choice of catalyst, base, and solvent was crucial for the reactivity and selectivity of these processes.
