- Enantioselective synthesis of α-trifluoromethyl arylmethylamines by ruthenium-catalyzed transfer hydrogenation reaction
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A simple combination of dichloro(para-cymene)ruthenium(II) dimer, a chiral amino alcohol and isopropyl alcohol allowed for in-situ generation of the bifunctional catalyst responsible for the transfer hydrogenation reaction of trifluoromethyl ketimines in excellent yields with high enantioselectivities (up to 93% ee). Herein, we describe the optimization, scope, limitations, and applications of the method.
- Dai, Xiaoyang,Cahard, Dominique
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p. 1317 - 1328
(2014/05/06)
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- Expedient trimethylaluminium-promoted one-pot synthesis of functional heteroaromatic and carbocyclic trifluoroethylamines
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The synthesis of trifluoroethylamines as amide bond mimics is an interesting topic in current research. They are well known tools in pharmaceutical and agrochemical industry. Other methods described in literature are often restricted to few substrates. We herein report a new synthetic approach towards this class of substances. First, the trimethylaluminium- promoted generation of a trifluoromethyl-ketimine from the corresponding trifluoromethyl ketone and an aniline derivative was investigated. Next, the ketimine was converted into the trifluoroethylamines in a one-pot reaction by simple addition of borane-methyl sulfide complex.
- Allendoerfer, Nadine,Sudau, Alexander,Braese, Stefan
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experimental part
p. 2815 - 2824
(2010/12/29)
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- Nucleophilic trifluoromethylation of imines under acidic conditions
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A general method for the trifluoromethylation of imines by using Me 3SiCF3 under acidic conditions is described. The reaction is promoted by hydrofluoric acid generated in situ from KHF2 and either TFA or TfOH. A new chemoselectivity pattern was achieved, as the C=N bond was found to be more reactivate than the carbonyl group. The trifluoromethylation reaction is believed to proceed by concerted transfer of the CF3 group from the silicon atom to the iminium electrophile. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Levin, Vitalij V.,Dilman, Alexander D.,Belyakov, Pavel A.,Struchkova, Marina I.,Tartakovsky, Vladimir A.
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supporting information; experimental part
p. 5226 - 5230
(2009/06/06)
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