- Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes
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The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.
- Cloutier, Mélissa,Roudias, Majdouline,Paquin, Jean-Fran?ois
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p. 3866 - 3870
(2019/05/24)
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- Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3at room temperature
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A novel Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3has been developed for the construction of Csp-CF3bond under mild conditions. This method proceeds smoothly at room temperature and shows a widely functional compatibility, providing a series of corresponding trifluoromethylated acetylenyl-containing aromatics in good yields.
- Yang, Lingling,Jiang, Linlin,Li, Yaming,Fu, Xinmei,Zhang, Rong,Jin, Kun,Duan, Chunying
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p. 3858 - 3862
(2016/07/06)
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- Cu-promoted oxidative trifluoromethylation of terminal alkynes with difluoromethylene phosphobetaine
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Difluoromethylene phosphobetaine (Ph3P+CF 2CO2-, PDFA), a known difluorocarbene reagent, was found to be able to efficiently trifluoromethylate terminal alkynes in the presence of Cu(I) and potassium fluoride. The transformation proceeded smoothly to afford the corresponding trifluoromethylated acetylenes in moderate yields. A difluorocarbene precursor, difluoromethylene phosphobetaine (Ph 3P+CF2CO2-, PDFA) was found to be able to act as a trifluoromethylating reagent in the presence of fluoride. The oxidative trifluoromethylation of terminal alkynes with PDFA promoted by Cu(I) occurred smoothly to give the corresponding trifluoromethylated acetylenes in moderate yields. Copyright
- Deng, Xiaoyun,Lin, Jinhong,Zheng, Jian,Xiao, Jichang
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p. 689 - 693
(2014/10/15)
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- Practical methods for the synthesis of trifluoromethylated alkynes: Oxidative trifluoromethylation of copper acetylides and alkynes
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Two practical and complementary methods are reported for the synthesis of trifluoromethylated alkynes. The first one, a mix-and-stir process, is based on the oxidative trifluoromethylation of readily available and bench-stable copper acetylides while the second one, which displays a broad substrate scope and has several advantages over existing procedures, is based on the oxidative copper-catalyzed direct trifluoromethylation of terminal alkynes. Both reactions provide user-friendly processes for the synthesis of trifluoromethylated acetylenes which can be easily obtained from readily available starting materials.
- Tresse, Cedric,Guissart, Celine,Schweizer, Stephane,Bouhoute, Yassine,Chany, Anne-Caroline,Goddard, Mary-Lorene,Blanchard, Nicolas,Evano, Gwilherm
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supporting information
p. 2051 - 2060
(2014/07/07)
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- Copper-mediated trifluoromethylation of terminal alkynes by S-(trifluoromethyl)diarylsulfonium salt
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The copper-mediated trifluoromethylation of terminal alkynes with S-(trifluoromethyl)diarylsulfonium salt has been carefully investigated. The reactions proceeded smoothly to afford trifluoromethylated acetylenes in moderate to good yields. This approach is a convenient method to synthesize a variety of functional trifluoromethylated acetylenes. A convenient method for the trifluoromethylation of a variety of terminal alkynes with S-(trifluoromethyl)diarylsulfoniumtriflate in the presence of copper iodide was described. The reactions proceeded smoothly under mild condition to give the desired product in moderate to good yields. Copyright
- Wang, Xiaoping,Lin, Jinhong,Zhang, Chengpan,Xiao, Jichang,Zheng, Xing
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p. 915 - 920
(2013/08/23)
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- Synthesis of trifluoromethylated acetylenes via copper-catalyzed trifluoromethylation of alkynyltrifluoroborates
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A new method for the synthesis of trifluoromethylated acetylenes is developed which involves the copper-catalyzed trifluoromethylation of alkynyltrifluoroborates with an electrophilic trifluoromethylating reagent. This method offers significant advantages such as efficiency and mild and base-free reaction conditions. A plausible mechanism is proposed.
- Zheng, Huidong,Huang, Yuanyuan,Wang, Zhiwei,Li, Huaifeng,Huang, Kuo-Wei,Yuan, Yaofeng,Weng, Zhiqiang
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supporting information
p. 6646 - 6649
(2013/01/15)
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- Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with Me3SiCF3
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An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me3SiCF3) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO2Et, -Br, and -NO2 were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful method to prepare trifluoromethylated acetylenes.
- Chu, Lingling,Qing, Feng-Ling
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supporting information; experimental part
p. 7262 - 7263
(2010/08/07)
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