- Metal-Free Activation of C-I Bonds and Perfluoroalkylation of Alkenes with Visible Light Using Phosphine Catalysts
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An efficient metal-free, photomediated iodo perfluoroalkylation under mild conditions was developed. Using catalytic amounts (10 mol %) of phosphines and blue light irradiation, various olefins are transformed into the corresponding addition products with
- Helmecke, Lucas,Spittler, Michael,Baumgarten, Kai,Czekelius, Constantin
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Read Online
- Semi-perfluoroalkylated perylene diimides for conjugated polymers with high molecular weight and high electron mobility
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Perylene diimides (PDIs) and their derivatives are excellent semiconductors, while conjugated polymers based on PDIs have limited applications because of their low electron mobility (μe) derived from low molecular weight. The reported maximum number-average molecular weight (Mn) of related polymers is only 21 kDa because PDIs have very poor solubility due to strong π–π stacking of their big planar conjugated cores. Herein, it is found that suitable semi-perfluoroalkyl groups could enhance the solubility of PDIs significantly, and a series of semi-perfluoroalkyl modified conjugated polymers with high molecular weight and electron mobility were synthesized. The maximum Mn reaches 94.8 kDa [P(4CF8CH-PDI-T2)HW]. In their space-charge-limited current (SCLC) devices, all polymers exhibit typical characters of electron transporting semiconductors, and the highest μe is up to 8.40 × 10?3 cm2?V?1?s?1 [P(4CF8CH-PDI-T2)HW], which is similar as that of widely used electron transporting semiconductor PC61BM (6.41 × 10?3?cm2?V?1?s?1).
- Cai, Chunsheng,Wan, Ji,Zhang, Youdi,Yuan, Zhongyi,Huang, Qingfang,Xu, Guodong,Hu, Yu,Zhao, Xiaohong,Chen, Yiwang
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- Triethylborane-induced radical addition of halogenated compounds to alkenes and alkynes in water
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Treatment of a mixture of α-iodo-γ-butyrolactone and phenylacetylene in water with a catalytic amount of triethylborane provided the corresponding adduct in good yield via intermolecular radical addition reaction. The triethylborane-mediated radical react
- Nakamura,Yorimitsu,Shinokubo,Oshima
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- A general and green fluoroalkylation reaction promoted: Via noncovalent interactions between acetone and fluoroalkyl iodides
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The first example of visible light promoted fluoroalkylation reactions initiated via noncovalent interactions between acetone and fluoroalkyl iodides is presented. The reaction system features synthetic simplicity, mild reaction conditions without any photoredox catalyst, and high functional group tolerance. A wide range of substrate scopes such as alkenes, alkynes and (hetero)arenes were all compatible with the reaction system.
- Mao, Ting,Ma, Ming-Jian,Zhao, Liang,Xue, De-Pu,Yu, Yanbo,Gu, Jiwei,He, Chun-Yang
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supporting information
p. 1815 - 1818
(2020/02/20)
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- Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate
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Two efficient continuous flow iodoperfluoroalkylation methods are described: using 0.05 mol % perylene diimide (PDI) photocatalyst under 450 nm irradiation or substoichiometric triethylamine under 405 nm irradiation. These methods enable dramatically elevated productivity versus batch processes. The triethylamine-mediated method is explored mechanistically and in substrate scope. The gram-scale synthesis of an active pharmaceutical ingredient side chain is also reported in flow, via a photochemical iodoperfluoroalkylation followed by hydrogenolysis.
- Rosso, Cristian,Williams, Jason D.,Filippini, Giacomo,Prato, Maurizio,Kappe, C. Oliver
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supporting information
p. 5341 - 5345
(2019/07/03)
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- MANUFACTURING METHOD OF FLUOROALKANE
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PROBLEM TO BE SOLVED: To provide a manufacturing method of fluoroalkane capable of high purity fluoroalkane from inexpensive and easily available raw materials at high yield, and excellent in economical efficiency. SOLUTION: There is provided a manufacturing method of fluoroalkane for manufacturing Rf-CH2CH2CH2-Rh by reacting Rf-X and CH2=CHCH2-Rh in the presence of a reaction initiator to obtain Rf-CH2CHXCH2-Rh, and reducing the same in the presence of a noble metal catalyst and an inorganic compound. In the formula, Rf represents a fluorine-containing alkyl group having 2 to 12 carbon atoms, Rh represents an alkyl group having 2 to 12 carbon atoms, and X represents a bromine atom or an iodine atom. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0027
(2019/08/12)
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- METHOD FOR PRODUCING FLUORINATED COMPOUND
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This invention solves the problem of providing an efficient, new method for producing a fluoromethylene-containing compound. The problem can be solved by a method for producing a compound represented by formula (1) or a ring-closed or ring-opened derivative of the compound, wherein R1 represents an organic group, RX represents hydrogen or fluorine, R2a, R2b, R2c, and R2d are the same or different, and each represents —Y—R21 or —N(—R22)2, or R2b and R2c may join together to form a bond, wherein Y represents a bond, oxygen, or sulfur, R21 represents hydrogen or an organic group, and R22, in each occurrence, is the same or different and represents hydrogen or an organic group; the method comprising step A of reacting a compound represented by formula (2), wherein X represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3), wherein the symbols are as defined above, in the presence of a reducing agent under light irradiation.
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Paragraph 0151; 0152; 0153; 0154-0156; 0157; 0177-0182
(2019/03/14)
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- Preparation method of high-purity straight-chain perfluoroalkyl iodoalkane
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The invention discloses a preparation method of high-purity straight-chain perfluoroalkyl iodoalkane. The method is characterized by taking perfluoroalkyl iodine and alkene as reaction substrates, andcarrying out addition reaction in the presence of an initiator and additives. Through the method, the initiator and alkene are simultaneously added into a reaction system, so that the generation of free radicals is synergistic with the addition reaction; the generation of addition branched-chain isomers is reduced; the generation of branched-chain isomers is reduced; the yield of the finally prepared perfluoroalkyl iodoalkane is about 97.5%; the purity of the prepared perfluoroalkyl iodoalkane is about 99%; the method is suitable for industrial production.
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Paragraph 0030; 0031
(2018/09/08)
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- PROCESS FOR THE PRODUCTION OF SEMIFLUORINATED ALKANES
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The present invention relates to a process for the production of semifluorinated alkanes.
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Page/Page column 25
(2018/11/26)
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- p-MeOC6H4N2+ BF4-/TiCl3: a novel initiator for halogen atom-transfer radical reactions in aqueous media
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With the combination of p-methoxybenzene-diazonium tetrafluoroborate with TiCl3 as the initiator, a wide range of halogen atom-transfer radical addition or cyclization reactions could be efficiently implemented in aqueous solution at room tempe
- Cao, Lidong,Li, Chaozhong
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scheme or table
p. 7380 - 7382
(2009/04/14)
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- Oxidant-induced addition reaction of perfluoroalkyl halides to alkenes and alkynes
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Ceric sulfate, cerium (IV) ammonium nitrate, sodium persulfate, ammonium persulfate and potassium permanganate can smoothly induce the addition reaction of perfluoroalkyl halides (1) to electron-rich olefins (2) and alkynes (4) to give monoadducts (3 or 5
- Guo, Xiao-Chuan,Chen, Qing-Yun
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- Titanium-catalyzed addition of perfluoroalkyl iodides to alkenes
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Perfluoroalkyl iodides, in the presence of a catalytic amount of Ti0 generated in situ, add to alkenes in dimethoxyethane solvent to afford 1-(n-perfluoroalkyl)-2-iodoalkanes in moderate to good yields. 1-Alkenes, 1-alkynes and alkenes containi
- Davis, Charles R.,Burton, Donald J.,Yang, Zhen-Yu
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p. 135 - 140
(2007/10/02)
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- A NEW TIN(II) CHLORIDE-SILVER(I) ACETATE OR -LEAD(II) BROMIDE REAGENT FOR THE ADDITION OF F-ALKYL IODIDES TO ALKENES
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A tin(II) chloride-silver(I) acetate or tin(II) chloride-lead(II) bromide reagent can efficiently promote the addition of F-alkyl iodides to various alkenes in anhydrous methanol at room temperature to afford the corresponding F-alkylated iodides in fairl
- Ishihara, Takashi,Kuroboshi, Manabu
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p. 1611 - 1618
(2007/10/02)
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- Addition Reactions of F-Alkyl Iodides to Carbon-Carbon Double Bonds Promoted by Metallic Tin(0)-Metal Salt System
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F-Alkyl iodides readily reacted with a variety of alkenes in methanol at room temperature under the influence of metallic tin(0)-silver(I) acetate or metallic tin(0)-copper(I) chloride to afford the corresponding addition products, F-alkylated iodides, in
- Kuroboshi, Manabu,Ishihara, Takashi
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p. 299 - 304
(2007/10/02)
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- New Efficient Palladium-Catalyzed Perfluoroalkylation of Carbon-Carbon Multiple Bonds with F-Alkyl Iodides. An Expedient Route to F-Alkylated Alkyl and Alkenyl Iodides
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A variety of alkenes and alkynes efficiently undergo the perfluoroalkylation with F-alkyl iodides in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) in hexane to give good yields of the corresponding F-alkylated alkyl and al
- Ishihara, Takashi,Kuroboshi, Manabu,Okada, Yoshiji
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p. 1895 - 1896
(2007/10/02)
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