- Synthesis of gem-difluoroalkenes by copper-catalyzed regioselective hydrodefluorination of 1-trifluoromethylalkenes
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A copper-catalyzed regioselective hydrodefluorination of 1-trifluoromethylalkenes with hydrosilanes has been developed. The copper catalysis is compatible with several functional groups, including alkyl chloride, ether, ester, nitrile, and imide moieties, to form the corresponding gem-difluoroalkenes in good yields. Additionally, asymmetric induction is also possible by using the chiral DTBM-SEGPHOS ligand, and gem-difluoroalkene with point chirality at the allylic position is obtained with high enantioselectivity.
- Hirano, Koji,Kojima, Yuki,Miura, Masahiro,Takata, Tatsuaki
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- Stereoselective formation of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes with lithium organoborates
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A method for stereoselective construction of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes in mild conditions was described. The combination of lithium organoborate and ZnBr2 generated in situ lithium ar
- Huang, Weichen,Shen, Qilong,Xiao, Yisa
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supporting information
(2022/02/02)
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- Palladium-Catalyzed Carbonylative Cross-Coupling of Difluoroalkyl Halides with Alkylboranes under 1 atm of CO
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A palladium catalyzed carbonylative cross-coupling of difluoroalkyl halides with alkyl-9-BBN under 1 atm of CO has been developed. The reaction shows broad substrate scope and high functional group tolerance, even toward complex pharmaceuticals, providing
- Zhang, Xingang,Zhao, Hai-Yang,Zhou, Minqi
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p. 9106 - 9111
(2021/12/06)
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- Copper(I)-catalyzed stereoselective defluoroborylation of aliphatic gem-difluoroalkenes
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This study reports a method for the stereoselective copper(I)catalyzed defluoroborylation of aliphatic gem-difluoroalkenes to afford (Z)-monofluoro-substituted borylalkenes. Gem-difluoro-alkenes bearing a variety of functional groups were efficiently borylated with high stereoselectivity. A theoretical study of the reaction mechanism is also described.
- Ito, Hajime,Seo, Tamae,Kojima, Ryoto,Kubota, Koji
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supporting information
p. 1330 - 1332
(2018/10/15)
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- Heterogeneous Catalytic Hydroarylation of Olefins at a Nanoscopic Aluminum Chlorofluoride
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We report on hydroarylation reactions of arenes with olefins under very mild conditions catalyzed heterogeneously by aluminum chlorofluoride (ACF; AlClxF3?x, x≈0.05–0.25). The reactions of benzene and toluene with ethylene or propylene proceed with high conversions to afford various alkylated arenes. For cyclohexene and 1-hexene, the reactions require higher temperatures and the conversions are lower. ACF also catalyzes the hydroarylation of 1,3,5-trifluorobenzene and pentafluorobenzene with ethylene and propylene. The alkylations of arenes with non-fluorinated olefins resemble typical Friedel–Crafts chemistry to give rise to Markovnikov regioselectivity. The reaction of CF3CH=CH2 with benzene proceeds with anti-Markovnikov regioselectivity to give the fluorinated olefin PhCHCH=CF2 and the alkylation product PhCH2CH2CF3 as products of C?F and C?H activation.
- Calvo, Beatriz,Wuttke, Jan,Braun, Thomas,Kemnitz, Erhard
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p. 1945 - 1950
(2016/07/06)
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- Catalytic C-F activation via cationic group IV metallocenes
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The catalytic cleavage of sp3 C-F bonds of 3,3,3-trifluoropropene (TFP) can be performed using cationic group IV metallocenes and an excess of triisobutylaluminum. The isobutyl adduct 1,1-difluoro-5-methyl-hex-1-ene (DFMH) as well as 3,3-(diflu
- Lanzinger, Dominik,H?hlein, Ignaz M.,Wei?, Sebastian B.,Rieger, Bernhard
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supporting information
p. 21 - 28
(2015/02/19)
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- Difluorophenylsulfanylmethyl radical and difluoromethylene diradical synthons: gem-difluoromethylene building block
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Bromodifluorophenylsulfanylmethane has been demonstrated to be a highly versatile gem-difluoromethylene (CF2) building block via the reaction of difluorophenylsulfanylmethyl radical with olefins. gem-Difluoroalkenes and products containing a mi
- Reutrakul, Vichai,Thongpaisanwong, Thanchanok,Tuchinda, Patoomratana,Kuhakarn, Chutima,Pohmakotr, Manat
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p. 6913 - 6915
(2007/10/03)
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- REACTION OF 3,3,3-TRIFLUOROPROPENE WITH BENZENE OVER Al2O3 TREATED WITH CF3Cl
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The reaction between 3,3,3-trifluoropropene and benzene in a vapor phase was carried out over various Al2O3.Trifluoropropylbenzene was obtained selectively when CF3Cl-treated Al2O3 was used as a catalyst.
- Takusari, Hisanori,Okazaki, Susumu
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p. 885 - 888
(2007/10/02)
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