- Copper-catalyzed cascade radical cyclization of alkynoates: Construction of aryldifluoromethylated coumarins
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A mild and simple method is reported for the construction of 3-difluoroarylmethylated coumarins using α,α-difluoroarylacetic acids as an easily handled difluoromethyl source in reaction with ester 3-arylpropiolates under the promotion of copper. The reaction involves a proposed radical-triggered domino decarboxylative aryldifluoromethylation/5-exo cyclization/ester migration process that directly forms Csp2-CF2Ar and C-C bonds with good functional group tolerance. This journal is
- Chen, Zhiwei,Huang, Xiaoxiao,Tang, Wei,Zeng, Piaopiao
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supporting information
p. 10223 - 10227
(2021/12/10)
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- Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds
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An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.
- Wang, Pingyang,Du, Pengcheng,Sun, Qianqian,Zhang, Jianhua,Deng, Hongmei,Jiang, Haizhen
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p. 2023 - 2029
(2021/03/16)
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- Synthetic method of aromatic ring group or aromatic heterocyclic tetrazole
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The synthetic method comprises the following steps: (1) reacting 1.0 eq of ArI or HArI with 1.2 eq of ethyl 2, 2-difluoroacetate in the presence of DMSO as a solvent and 4.0 eq of Cu under the protection of nitrogen at 30 DEG C and 50 DEG C, and purifying to obtain a first intermediate compound; (2) dissolving 1.0 eq of the first intermediate compound in a mixed solvent of THF and water, adding 2.0 eq of LiOH, reacting at room temperature for 2 hours, spin-drying the solvent, adding HCl until the pH value is equal to 3, and filtering to obtain a second intermediate compound; and (3) reacting 1.0 eq of the second intermediate compound with 2.0 eq of diphenyl azide phosphate in the presence of 2.5 eq of triethylamine by taking tert-butyl alcohol as a solvent to generate aromatic ring group or aromatic heterocyclic tetrazole. The invention provides a novel synthetic method of aromatic ring group or aromatic heterocyclic tetrazole, wherein a target compound can be more conveniently obtained, and reagents participating in the reaction are low in toxicity, mild in reaction condition, simple and safe in aftertreatment, good in product quality and suitable for large-scale production.
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Paragraph 0055-0062; 0065
(2020/12/30)
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- Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids
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A facile Fe(III)-catalyzed oxidative decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with coumarins has been developed. This transformation, which provides a series of C-3 difluoroarylmethylated coumarins containing various functional groups in moderate-to-good yields, features easily accessible starting materials and operational simplicity.
- Chen, Zhiwei,Bai, Xiang,Sun, Jie,Xu, Yicheng
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supporting information
p. 7674 - 7682
(2020/07/15)
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- Silver-Catalyzed Decarboxylative Alkynylation of α,α-Difluoroarylacetic Acids with Ethynylbenziodoxolone Reagents
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A decarboxylating alkynylation of α,α-difluoroarylacetic acids with ethynylbenziodoxolone reagents is reported. AgNO3 serves as the catalyst and K2S2O8 as the oxidant. A series of functional groups were tolerated, and moderate to good yields were obtained.
- Chen, Fei,Hashmi, A. Stephen K.
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supporting information
p. 2880 - 2882
(2016/07/06)
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- Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination
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An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.
- Shao, Changdong,Shi, Guangfa,Zhang, Yanghui
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p. 5529 - 5538
(2016/11/25)
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- ADENOSINE A3 RECEPTOR MODULATING COMPOUNDS AND METHODS OF USE THEREOF
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Provided herein is a method of preventing, treating, or ameliorating one or more symptoms of an adenosine A3-mediated condition, disorder, or disease, with a compound of Formula I. Also provided herein is a method of preventing, treating, or ameliorating one or more symptoms of glaucoma or ocular hypertension. Further provided herein is a method of modulating the activity of an adenosine A3 receptor.
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- Fluorination of 2-oxo-ethane derivatives with diethylaminosulfur trifluoride (DAST)
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The fluorination of 2-oxo-ethane derivatives with DAST is described. The use of Znl2 as a catalyst improves the yield in the fluorination of 2-phenyl-2-oxo-acetonitrile with DAST.
- Haegele, Gerhard,Haas, Andreas
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