- Novel synthesis of perfluoroalkylated heterocyclic compounds from α-chlorostyrenes via perfluoroalkylated α,β-unsaturated ketones
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A convenient method for the one-pot synthesis of heterocyclic compounds bearing a perfluoroalkyl group from α-chlorostyrenes via perfluoroalkylated α,β-unsaturated ketones has been developed.
- Ohkoshi, Masanori,Yoshida, Masato,Matsuyama, Haruo,Iyoda, Masahiko
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- Cobalt-Catalyzed Hydroxyperfluoroalkylation of Alkenes with Perfluoroalkyl Bromides and Atmospheric Oxygen
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A mild and efficient method for the cobalt-catalyzed hydroxyperfluoroalkylation of alkenes has been developed. This method demonstrated broad substrate scope, good yields, and mild conditions with the tolerance of mono-, di-, and trisubstituted alkenes including both styrenes and non-activated aliphatic olefins. This strategy offered a valuable solution for rapid and efficient construction of β-perfluoroalkyl alcohols using widely available and inexpensive perfluoroalkyl bromides and atmospheric oxygen.
- Sun, Qilin,Pang, Liangzhi,Mao, Shuxian,Fan, Wu,Zhou, Yuyi,Xu, Jing,Li, Suhua,Li, Qiankun
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p. 1353 - 1364
(2021/12/02)
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- Oxygenative perfluoroalkylation of olefinic compounds using perfluoroalkyl iodide in the presence of oxygen
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Reactions of perfluoroalkyl iodides with styrene and its derivatives were investigated under radical conditions in the presence of oxygen. The photochemical reaction of styrene with CF3(CF2)5I in the presence of tributyltin hydride or tris(trimethylsilyl)silane under an oxygen atmosphere afforded the corresponding perfluoroalkylated alcohols in moderate yields together with CF3(CF2)5H. However, the photochemical reactions of styrene and its derivatives with CF3(CF2)nI (n = 3, 5) in the presence of hexabutylditin under oxygen produced the perfluoroalkylated alcohols in good yields. Furthermore, the reactions of styrenes with CF3(CF2)nI (n = 3, 5, 9) and Na2S2O4 in the presence of a base under air formed the same alcohols in good yields. The alcohols were found to provide a novel type of α-fluoroalkylated styrenes by acidic dehydration. Perfluoroalkylated α,β-unsaturated ketones were synthesized by oxygenative perfluoroalkylations of α-chlorostyrene and its derivatives using CF3(CF2)nI (n = 3, 5) under radical reaction conditions. The ketones were found to be good synthetic building blocks for perfluoroalkylated heterocycles, such as pyrazoles, dihydrodiazepines, pyrimidines, and isoxazoles.
- Yoshida, Masato,Ohkoshi, Masanori,Muraoka, Tsunehiro,Matsuyama, Haruo,Iyoda, Masahiko
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p. 1833 - 1842
(2007/10/03)
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- Synthesis of 3-perfluoroalkyl-, including 3-trifluoromethyl-, substituted pyrazoles from perfluoroalkylacetylenes
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3-Perfluoroalkylpyrazoles 2 have been prepared in excellent yield by the reactions of perfluoroalkylacetylenes 1 with hydrazine monohydrate under mild conditions. - Keywords: Perfluoroalkylpyrazoles; Synthesis; Perfluoroalkylacetylenes; Hydrazene; Nucleop
- Tang, Xiao-Qing,Hu, Chang-Ming
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p. 129 - 132
(2007/10/02)
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- Synthese des F-alkylpyrazoles: Identification par RMN de 19F et comparaison avec les homologues hydrocarbones
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In this paper, we report the synthesis of forty new pyrazoles substituted by one or more perfluoroalkyl chains.These compounds were obtained by condensation of a hydrazine (substituted or not) on an F-alkyl β-diketone.Unlike hydrocarbon chemistry, a react
- Peglion, Jean-Louis,Pastor, Raphael-Emile,Cambon, Aime-Roger
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p. 309 - 315
(2007/10/02)
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