1401715-73-8Relevant articles and documents
Cu(II)-Mediated Decarboxylative Trifluoromethylthiolation of α,β-Unsaturated Carboxylic Acids
Cheng, Zhi-Fei,Tao, Ting-Ting,Feng, Yi-Si,Tang, Wei-Ke,Xu, Jun,Dai, Jian-Jun,Xu, Hua-Jian
, p. 499 - 504 (2018)
A tunable method for the direct trifluoromethylthiolation of α,β-unsaturated carboxylic acids was developed to afford trifluoromethylthiolated ketones or alkenes. The reaction proceeds smoothly under mild conditions and shows an excellent functional group tolerance.
Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis
Arimori, Sadayuki,Takada, Masahiro,Shibata, Norio
, p. 19456 - 19459 (2015)
Trifluoromethylsulfinyl and trifluoromethylthio groups are both important substituents for pharmaceuticals, agrochemicals and functional materials. We herein report the trifluoromethylthiolation of allyl alcohols 2 with trifluoromethanesulfonyl hypervalent iodonium ylide 1 under copper catalysis to provide trifluoromethylsulfinyl compounds 3. Trifluoromethylthiolation of boronic acids 4 with 1 furnished trifluoromethylthio compounds 5.
Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis
Honeker, Roman,Garza-Sanchez, R. Aleyda,Hopkinson, Matthew N.,Glorius, Frank
, p. 4395 - 4399 (2016)
Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical.
Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF3for (E)-Vinyl Trifluoromethyl Thioethers
Fang, Ge,Hong, Jianquan,Huang, Shuai,Jiang, Chao,Liu, Yang,Zhang, Wei,Zheng, Changge
supporting information, (2020/07/03)
An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct Cvinyl-SCF3 bonds with stable AgSCF3 as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.
N-Trifluoromethylthio-dibenzenesulfonimide: A Shelf-Stable, Broadly Applicable Electrophilic Trifluoromethylthiolating Reagent
Zhang, Panpan,Li, Man,Xue, Xiao-Song,Xu, Chunfa,Zhao, Qunchao,Liu, Yafei,Wang, Haoyang,Guo, Yinlong,Lu, Long,Shen, Qilong
, p. 7486 - 7509 (2016/09/09)
The super electrophilicity of a shelf-stable, easily prepared trifluoromethylthiolating reagent N-trifluoromethylthio-dibenzenesulfonimide 7 was demonstrated. Consistent with the theoretical prediction, 7 exhibits reactivity remarkably higher than that of other known electrophilic trifluoromethylthiolating reagents. In the absence of any additive, 7 reacted with a wide range of electron-rich arenes and activated heteroarenes under mild conditions. Likewise, reactions of 7 with styrene derivatives can be fine-tuned by simply changing the reaction solvents to generate trifluoromethylthiolated styrenes or oxo-trifluoromethylthio or amino-trifluoromethylthio difunctionalized compounds in high yields.
