- Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling
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Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst tBuBrettPhos Pd G3 and Cs2CO3 in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and-poor (hetero)arenes. The method provides access to 18F-labeled trifluoroethyl ethers by cross-coupling with [18F]trifluoroethanol.
- Szpera, Robert,Isenegger, Patrick G.,Ghosez, Maxime,Straathof, Natan J. W.,Cookson, Rosa,Blakemore, David C.,Richardson, Paul,Gouverneur, Véronique
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supporting information
p. 6573 - 6577
(2020/09/02)
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- Production method of flecainide
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The invention belongs to the technical field of compound synthesis, and particularly relates to a production method of flecainide, which comprises the following steps: 1) etherification reaction, 2) acetylation reaction, 3) oxidation reaction and 4) refining. According to the production method, qualified flecainide is synthesized through three steps, the process steps are simplified, the process operation is simple, the etherification reaction, the acetylation reaction and the oxidation reaction are adopted, so that the flecainide yield is stable, the yield is high, the impurity separation iseasily achieved, and the impurity operation is simple and convenient.
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Paragraph 0048-0050; 0054; 0059; 0063; 0066; 0068; 0072; 007
(2020/05/01)
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- Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
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A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.
- Chen, Zhixiang,Jiang, Yongwen,Zhang, Li,Guo, Yinlong,Ma, Dawei
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supporting information
p. 3541 - 3549
(2019/02/26)
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- A practical ligand-free copper(I) bromide-catalyzed fluoroalkoxylation of unactivated aryl bromides
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An efficient ligand-free fluoroalkoxylation of unactivated aryl bromides has been developed, with special attention focused on practicability of the reaction. Without precious metal and organic ligand, the reaction was carried out under the catalytic system of inexpensive copper(I) bromide as a catalyst, N,N-dimethyl formamide as a cocatalyst, and the corresponding stoichiometric sodium fluoroalkoxide as a nucleophilic reagent. The facile approach avoids the drawbacks associated with cost, separation and pollution of ligand to enable sustainable access to aryl fluoroalkyl ethers from readily available bromoarenes.
- Guo, Ying,Li, Yu-Dao,Chen, Cheng,Zhao, Jian-Hong,Liu, Hong-Wei,Liao, Dao-Hua,Ji, Ya-Fei
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p. 2525 - 2537
(2016/03/16)
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- Facile access to fluorinated aryl and vinyl ethers through copper-catalysed reaction of fluoro alcohols
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Fluorinated alcohols react with aryl and vinyl halides by copper-catalysed cross-coupling reactions to afford the corresponding ethers. With trifluoroethanol (TFE) the reaction proceeds with both iodides and bromides and a wide range of aromatic substituents are tolerated. When higher fluorinated homologues such as C7P15CH2OH were used, the corresponding products were obtained in good yields, thus of-fering an interesting entry to fluorous tagging.
- Vukga, Daniela,Legros, Juelien,Crousse, Benoit,Bonnet-Delpon, Daniele
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experimental part
p. 3513 - 3518
(2009/12/01)
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- α,α-dibromo-α-chloro-acetophenones as synthons
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This disclosure relates to the use of α,α-dibromo-α-chloroacetophenone compounds as intermediates for the preparation of aromatic carbonyl compounds, especially aromatic amides. The compound 2,5-bis(2,2,2-trifluoroethoxy)-α,α-dibromo-α-chloroacetophenone is especially useful as an intermediate for the preparation of flecainide, a known pharmaceutical.
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- Processes for preparing pentafluoroethoxy- and pentafluoroethylthiobenzene drivatives
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A process for the preparation of (pentafluoroethoxy)- and (pentafluoroethylthio)benzene derivatives either from phenol, thiophenol or from halobenzene. A halobenzene is reacted with trifluoroethanol or a phenol or a thiophenol is reacted with a compound of the formula CF3 --CH2 --O--R'. The product is chlorinated and the chlorinated product is fluorinated in liquid hydrofluoric acid in the presence of a Lewis acid. The compounds obtained by the process of the present invention are used as synthesis intermediates in the phytosanitary, pharmaceutical and veterinary industries, and are used in lubricants.
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- Process for the preparation of derivatives of pyrrolidine and piperidine
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Processes and intermediates for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.
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- Process for the preparation of derivatives of piperidine
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Processes for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.
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- Acid-Catalyzed Reaction of 2,2,2-Trifluorodiazoethane for Analysis of Functional Groups by 19F Nuclear Magnetic Resonance Spectrometry
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The acid-catalyzed reactions of trifluorodiazoethane with alcohols, phenols, thiols, and carboxylic acids are reported.The yield data for these trifluoroethyl derivatives suggest a simple, and in many cases, quantitative method for introduction of a fluorine tagging group.The 19F chemical shifts indicate that most functional groups (e.g., phenols, alcohols, etc.) have fairly well resolved chemical shifts regions.In addition, paramagnetic shift reagents have been utilized to selectively differentiate carboxylic acids from other active hydrogen functional groups.
- Koller, K. L.,Dorn, H. C.
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p. 529 - 533
(2007/10/02)
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