- The trifluoromethylation of 1,1-dibromo-1-alkenes using trifluoromethylcopper (CF3Cu) generated in situ from methyl fluorosulfonyldifluoroacetate
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The trifluoromethylation of 2-aryl-1,1-dibromo-1-alkenes with CF3Cu under palladium catalysis gave bistrifluoromethylated compounds (2), whereas under the same reaction conditions, monotrifluoromethylated products (3) were obtained exclusively
- Qing,Zhang,Peng
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- Controlled trifluoromethylation reactions of alkynes through visible-light photoredox catalysis
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The control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3-containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF 3I by environmentally benign and efficient visible-light photoredox catalysis. Subtle differences in the combination of catalyst, base, and solvent enabled the control of reactivity and selectivity for the reaction between an alkyne and CF3I. Variety through selectivity: Highly valuable trifluoromethylated alkenyl iodides, alkenes, and alkynes were selectively generated from alkynes and CF3I by environmentally benign and efficient visible-light photoredox catalysis. A suitable choice of catalyst, base, and solvent was crucial for the reactivity and selectivity of these processes.
- Iqbal, Naeem,Jung, Jaehun,Park, Sehyun,Cho, Eun Jin
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supporting information
p. 539 - 542
(2014/01/23)
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- Synthesis, structure, and thermolysis of a novel spirotellurane bearing two 1,2-oxatelluretane rings, 1,5-dioxa-4λ4-telluraspiro[3.3]heptane: Oxirane and olefin formation reactions
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The first 1,5-dioxa-4λ4-telluraspiro[3.3]heptane was synthesized and its structure was determined by X-ray analysis. This tellurane gave the corresponding oxirane and olefin, as well as alcohol, upon heating, which were shown to be formed via a radical pathway.
- Kano, Naokazu,Takahashi, Tatsuhisa,Kawashima, Takayuki
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p. 6775 - 6778
(2007/10/03)
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- Synthesis of Bis(trifluoromethyl)-Substituted Olefins: Methods of Preparation and Properties
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Several bis(trifluoromethyl)- and trifluoromethyl-substituted alkenes, dienes, arylalkenes, and α,β-unsaturated derivatives of carbonyl compounds such as tosylhydrazone 5b and diazomethane 5c were prepared.Their reactivity towards a variety of nucleophiles, resulting from the electron-withdrawing effect of the trifluoromethyl group, was investigated.Depending on the trifluoromethyl- and a bis(trifluoromethyl)-substituted double bond, different regioselectivities were observed in the reaction with morpholinocyclohexene as a nucleophile.An explanation is given on the basis of the 13C-NMR data. - Keywords: Trifluoromethyl-substituted alkenes; anti-Michael addition; Acceptor-substituted double bond; Steric demand of a CF3 group; Charge-shift correlation
- Haas, Alois,Lieb, Max,Zwingenberger, Joerg
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p. 2027 - 2036
(2007/10/03)
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- A General Method for the Preparation of 1,1-Bis(Trifluoromethyl)Substituted Olefins
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The title compounds are prepared by treatment of 1,1-difluoro-2-trifluoromethyl-1-alken-3-ols (1) with diethylaminosulfur trifluoride (DAST) with high regioselectivity.The alcohols (1) are obtained by the reaction of 2-pentafluoropropenyllithium with alde
- Lu, Hengyao,Burton, Donald J.
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p. 3973 - 3976
(2007/10/02)
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- Synthesis of Bis(trifluoromethyl)-Substituted Pyrethroids
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A method for the preparation of 1,1-bis(trifluoromethyl)-substituted pyrethroids is described.For this purpose, 1,1-bis(trifluoromethyl)-substituted olefins 9 are prepared by an easy method from the aldehydes 17 with 2,2-dichlorohexafluoropropane (16) and
- Mack, Helmut,Hanack, Michael
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p. 833 - 846
(2007/10/02)
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- A New Synthesis of 1,1-Bis(trifluoromethyl)-Substituted Alkenes
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1,1-Bis(trifluoromethyl)-substituted alkenes 6 are obtained by the reaction of aldehydes 5 with triphenylphosphine (4) and 2,2-dichlorohexafluoropropane (3) in modest to good yields.The alkenes 6 are not easily accessible by other routes.
- Hanack, M.,Korhummel, C.
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p. 944 - 947
(2007/10/02)
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