- Scalable Approach to Fluorinated Heterocycles with Sulfur Tetrafluoride (SF4)
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A general approach to fluorinated (hetero)aromatic derivatives is elaborated. The key reaction is a deoxofluorination of substituted acetophenones with sulfur tetrafluoride (SF4). In contrast to previous deoxofluorination methods, this transformation is fast, scalable (up to 70 g), and high-yielding. More than 100 novel or previously hardly accessible fluorinated heterocycles, interesting for medicinal chemistry and agrochemistry, were synthesized.
- Ahunovych, Volodymyr,Boretskyi, Andrii,Bugera, Maksym,Klipkov, Anton A.,Mykhailiuk, Pavel K.,Razhyk, Bohdan,Semenov, Sergey,Tarasenko, Karen,Trofymchuk, Serhii
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p. 12181 - 12198
(2021/09/13)
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- Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Br?nsted Base
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A copper catalyst in combination with N-fluorobenzenesulfonimide (NFSI) has been reported to functionalize benzylic C-H bonds to the corresponding benzylic sulfonimides via C-N coupling. Here, we reported a closely related Cu-catalyzed method with NFSI that instead leads to C-F coupling. This switch in selectivity arises from changes to the reaction conditions (Cu/ligand ratio, temperature, addition of base) and further benefits from inclusion of MeB(OH)2 in the reaction. MeB(OH)2 is shown to serve as a "redox buffer"in the reaction, responsible for rescuing inactive Cu(II) for continued promotion of fluorination reactivity.
- Buss, Joshua A.,Golden, Dung L.,Stahl, Shannon S.,Vasilopoulos, Aristidis
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supporting information
p. 5749 - 5752
(2020/10/02)
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- Copper-Mediated Aromatic 1,1-Difluoroethylation with (1,1-Difluoroethyl)trimethylsilane (TMSCF2CH3)
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A new method for the formation of 1,1-difluoroethyl copper species (“CuCF2CH3”) with 1,1-difluoroethylsilane (TMSCF2CH3) has been developed. The “CuCF2CH3” species can be applied to the efficient 1,1-difluoroethylation of diaryliodonium salts under mild conditions, affording (1,1-difluoroethyl)arenes in good to excellent yields. This convenient procedure tolerates a wide range of functional groups and thus serves as a practical synthetic tool for the introduction of CF2CH3 group(s) into complex molecules.
- Li, Xinjin,Zhao, Jingwei,Wang, Yunze,Rong, Jian,Hu, Mingyou,Chen, Dingben,Xiao, Pan,Ni, Chuanfa,Wang, Limin,Hu, Jinbo
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p. 1789 - 1792
(2016/07/07)
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- Benzobis(thiadiazole) derivative and organic electronics device comprising same
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A benzobis(thiadiazole) derivative represented by the formula (1): in which R represents a group containing at least one fluorine atom (with the proviso that fluorine atom (F) and trifluoromethyl group (—CF3) are excluded), and m represents an integer of from 1 to 10.
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Page/Page column 41
(2016/04/20)
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- METHOD FOR PRODUCING 1,1-DIFLUOROALKYL-AROMATIC COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing a 1,1-difluoroalkyl-aromatic compound, using an economical fluorinating agent which, when being handled, does not require any particular attention nor any special reactor. SOLUTION: Provided is an economical and safe method for producing a 1,1-difluoroalkyl-aromatic compound represented by formula (III) by reacting a [difluoro(trimethylsilyl)methyl]-aromatic compound represented by formula (I) (R1 represents a halogen group or a trimethylsilyl group) with a halogenated alkyl represented by formula (II) (R2 represents a C1-3 alkyl; and X represents a halogen group) in the presence of potassium fluoride. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0028
(2020/10/19)
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- 2-PYRIDONE COMPOUND
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This 2-pyridone compound represented by formula [1] or a tautomer of said compound, or a pharmaceutically acceptable salt of said compound or said tautomer, or a solvate of said compound or the like has a superior GK-activating effect and is useful as a p
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Paragraph 0110; 0111
(2015/11/16)
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- METALLOENZYME INHIBITOR COMPOUNDS AS FUNGICIDES
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The instant invention describes compounds of Formula I having metalloenzyme modulating activity, and methods of treating diseases disorders or symptoms thereof mediated by such metalloenzymes.
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Paragraph 00211
(2015/11/09)
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- BENZOBIS(THIADIAZOLE) DERIVATIVE AND ORGANIC ELECTRONICS DEVICE USING SAME
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The present invention relates to a benzobis(thiadiazole) derivative represented by the formula (1): wherein R represents a group containing at least one fluorine atom (with the proviso that fluorine atom (F) and trifluoromethyl group (-CF3) are excluded), and m represents an integer of from 1 to 10.
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Paragraph 0133; 0134
(2015/02/25)
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- Substituted 1-benzylcycloalkylcarboxylic acids and the use thereof
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The present application relates to novel substituted 1-benzylcycloalkylcarboxylic acid derivatives, to processes for their preparation, to their use for the treatment and/or prevention of diseases, and to their use for producing medicaments for the treatment and/or prevention of diseases, especially for the treatment and/or prevention of cardiovascular disorders.
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Page/Page column 34
(2012/07/14)
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- SUBSTITUTED PIPERIDINES
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The invention relates to novel substituted piperidines, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular disorders and tumour disorders.
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Page/Page column 34-35
(2011/02/18)
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- SUBSTITUTED PIPERIDINES
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The invention relates to novel substituted piperidines, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular diseases and tumour diseases.
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Page/Page column 26
(2010/12/29)
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