- Copper-Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate
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A copper-mediated trifluoroacetylation of various arenediazonium salts with ethyl trifluoropyruvate is reported. The reaction proceeded smoothly under mild conditions at room temperature giving trifluoromethyl aryl ketones in moderate to good yields. A variety of functional groups, including methoxy, hydroxy, ester, ketone, trifluoromethyl, and halide groups, were well tolerated. A possible reaction mechanism involving an aryl radical intermediate was proposed and supported by experimental evidence. This reaction provides a new route to trifluoromethyl aryl ketones, notable synthetic targets, from the corresponding anilines.
- Wu, Wei,Tian, Qinli,Chen, Taotao,Weng, Zhiqiang
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supporting information
p. 16455 - 16458
(2016/11/11)
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- Catalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines
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In the presence of a thiourea catalyst, β-CF3 nitroalkenes react with Hantzsch esters in a highly enantioselective fashion, giving a broad range of β-CF3 amine precursors with a tertiary stereocentre at the β-position. This reaction
- Martinelli, Emilie,Vicini, Anna Chiara,Mancinelli, Michele,Mazzanti, Andrea,Zani, Paolo,Bernardi, Luca,Fochi, Mariafrancesca
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p. 658 - 660
(2015/01/09)
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- A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation
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Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess-Martin, PDC, and Swern oxidation.
- Tanaka, Yusuke,Ishihara, Takashi,Konno, Tsutomu
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experimental part
p. 99 - 104
(2012/05/07)
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- A general method of halogenation for synthesis of α-halodifluoromethyl ketones and [18F]-labeled trifluoromethyl ketones
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A convenient general method of halogenations suitable for synthesis of α-halodifluoromethyl ketones is reported. Reaction of 2,2-difluoro-1-aryl-1-trimethylsiloxyethenes (difluoro silyl enol ethers) (2a-e) with halogens at low temperature (-30 to -78 °C) produced a high yield of α-halodifluoromethyl ketones (1a-j). This one-step simple method can be highly useful for synthesis of [18F]-labeled α-trifluoromethyl ketones.
- Prakash, G.K. Surya,Hu, Jinbo,Alauddin, Mian M.,Conti, Peter S.,Olah, George A.
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p. 239 - 243
(2007/10/03)
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- Process for preparing trifluoromethyl ketones
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A process is described for preparing trifluoromethyl ketones of the formula I STR1 where R has the given meanings, wherein an alcohol of the formula II STR2 is reacted with a compound of the formula IV where n has the given meaning.
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- Charge-Transfer Quenching of Triplet α-Trifluoroacetophenones
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The effects of ring substituents and of aromatic quenchers on the photoreduction by toluene of α,α,α-trifluoroacetophenone (AF3) have been measured.A plot of log kCT vs. ionization potential of the donor indicates that ΔGCT equals 22percent ΔG for the full electron transfer.A corresponding plot of log kCT vs. the triplet state reduction potential of ring-substituted AF3's, if analyzed as linear, would indicate that there is no intrinsic difference in reactivity between n,?* and ?,?* triplets but would also indicate that ΔGCT equals 42percent ΔG.The discrepancy between the 22 and 42percent is suggested to involve differing reactivities of n,?* and ?,?* triplets.If n,?* triplets are substantially more reactive, the plot vs. triplet reduction potential is expected to curve upward as the equilibrium population of n,?* triplet increases with substitution.
- Wagner, Peter J.,Lam, Henry M. H.
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p. 4167 - 4172
(2007/10/02)
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