- The 2,4-dimethyl-7-pentafluorosulfanyl-5-(trifluoromethyl)dibenzo[b,d] thiophenium trifluoromethanesulfonate: The SF5-analog of Umemoto salt
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The SF5-analog of the Umemoto salt was synthesized in just two steps by combining our recently reported SF5-biaryl synthesis, via Suzuki coupling with 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate, with Magnier's one-pot synthesis of dibenzothiophenium salts employing CF 3SO2Na and triflic anhydride. The trifluoromethylating power of this novel onium salt toward reactive arenes was tested in a survey study on small scale.
- Okazaki, Takao,Laali, Kenneth K.,Reddy, A. Srinivas
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- General catalytic methylation of amines with formic acid under mild reaction conditions
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A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines including [N-13C]-labelled drugs in good to excellent yields under mild conditions. Methylation made easy: A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines, including [N-13C]-labelled drugs, in good to excellent yields at mild conditions (see scheme; dppp=(1,3-bis(diphenylphosphino)propane)).
- Sorribes, Ivan,Junge, Kathrin,Beller, Matthias
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supporting information
p. 7879 - 7883
(2014/07/07)
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- A general catalytic methylation of amines using carbon dioxide
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Putting CO2 to work: Carbon dioxide is shown to be a general and selective methylating reagent for secondary and primary, aromatic and aliphatic amines under reductive conditions. A variety of tertiary amines are obtained from CO2 and commercially available silanes in high yields with good tolerance to nitrile, olefin, ether, ester, and hydroxy groups. Copyright
- Li, Yuehui,Fang, Xianjie,Junge, Kathrin,Beller, Matthias
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p. 9568 - 9571
(2013/09/23)
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- Silver-catalysed trifluoromethylation of arenes at room temperature
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A variety of heteroarenes and electron rich arenes can be trifluoromethylated at room temperature with TMSCF3, catalytic silver and PhI(OAc)2.
- Seo, Sangwon,Taylor, John B.,Greaney, Michael F.
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supporting information
p. 6385 - 6387
(2013/08/23)
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- A new method for the synthesis of trifluoromethylating agents-Diaryltrifluoromethylsulfonium salts
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A new synthetic method has been developed to prepare diaryltrifluoromethylsulfonium salts from diaryldifluorosulfuranes by the action of Me3SiCF3/F-. This reaction is the transformation of nucleophilic trifluoro-methylating reagent into electrophilic one.
- Yagupolskii, Lev M.,Matsnev, Andrej V.,Orlova, Raisa K.,Deryabkin, Boris G.,Yagupolskii, Yurii L.
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p. 131 - 136
(2008/09/21)
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- TRIFLUOROMETHYLATION OF AROMATIC AMINO AND THIO COMPOUNDS BY BISTRIFLUOROMETHYL TELLURIDE
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The reaction of aromatic and heterocyclic amines with (CF3)2Te gave the products from trifluoromethylation in the aromatic ring.The reaction with the corresponding thiols gave S-trifluoromethyl derivatives.
- Naumann, D.,Pazenok, S. V.,Turra, V.
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p. 128 - 130
(2007/10/02)
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- Photochemical Trifluoromethylation of Some Aromatic and Heteroaromatic Compounds with Trifluoromethyl Bromide
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The photochemical introduction of trifluoromethyl group with CF3Br in aromatic and heteroaromatic rings was investigated for 9 compounds.Naphthalene, anthracene, anisole, N,N-dimethylaniline, ferrocene, benzothiophene, isoquinoline, and N-methylpyrrole gave trifluoromethylated products in 6.5-100percent yields.In one step from uracil, a pharmacologically important 5-trifluoromethyluracil can be synthesized by this method in 11percent yield.Based on the mechanistic study carried out for the naphthalene-CF3Br-CH3CN system, the reaction is found to proceed via the electron transfer from an excited singlet state of naphthalene to CF3Br.
- Akiyama, Takeo,Kato, Kohji,Kajitani, Masatsugu,Sakaguchi, Yoshio,Nakamura, Junko,et al.
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p. 3531 - 3538
(2007/10/02)
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