41167-07-1Relevant academic research and scientific papers
Preparation method of flupiperidinol
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Paragraph 0089; 0095; 0098; 0104, (2021/03/24)
The invention belongs to the technical field of medicine preparation, and particularly relates to a preparation method of flupiperidinol. The preparation method of the fluoropiperidinol, provided by the invention, comprises the following steps of providing 4-(4-chlorphenyl)-4-piperidinol of which the purity is 99% or above, providing 4-chloro-1-(4-fluorophenyl)butan-1-one of which the purity is more than 99%, mixing the 4-(4-chlorphenyl)-4-piperidinol, 4-chloro-1-(4-fluorophenyl)butan-1-one, an alkaline substance and a catalyst, and carrying out a first substitution reaction to obtain a crudeproduct, and mixing the crude product with an organic solvent, and sequentially carrying out reflux and crystallization to obtain the flupiperidinol. The flupiperidinol prepared according to the preparation method provided by the invention has relatively high yield and purity.
Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis
Chen, Guangying,Cheng, Gui-Juan,Guo, Bin,Li, Xiaobao,Ran, Chongzhao,Wang, Lu,Wang, Ting,Wei, Jun-Jie,Zheng, Caijuan,Zheng, Chao
, p. 7543 - 7551 (2020/08/21)
Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C-H bonds, facilitating visible light-catalyzed construction of a variety of ketones. Tetrabutylammonium decatungstate and anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested a Pd0-PdII-PdIII-PdI-Pd0 pathway and revealed that regeneration of the Pd0 catalyst and the photocatalyst occurs simultaneously in the presence of KHCO3. This regeneration features a low energy barrier, promoting efficient coupling of the palladium catalytic cycle with the photocatalytic cycle. The work reported herein suggests great promise for further applications of HAT photocatalysis in palladium-catalyzed cross-coupling and C-H functionalization reactions to be successful.
Mn-Enabled Radical-Based Alkyl-Alkyl Cross-Coupling Reaction from 4-Alkyl-1,4-dihydropyridines
Wang, Jie,Pang, Yu-Bo,Tao, Na,Zeng, Run-Sheng,Zhao, Yingsheng
, p. 15315 - 15322 (2019/11/19)
Highly efficient alkylation of β-chloro ketones and their derivatives was achieved by means of domino dehydrochlorination/Mn-enabled radical-based alkyl-alkyl cross-coupling reaction. In situ-generated α,β-unsaturated ketones and their analogues were identified as the reaction intermediates. Known bioactive compounds, such as melperone and azaperone, could be easily prepared from β-chloropropiophenone in two steps.
Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals
Allen, Benjamin D. W.,Hareram, Mishra Deepak,Seastram, Alex C.,McBride, Tom,Wirth, Thomas,Browne, Duncan L.,Morrill, Louis C.
, p. 9241 - 9246 (2019/11/19)
A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.
Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids
Roslin, Sara,Odell, Luke R.
supporting information, p. 6895 - 6898 (2017/07/10)
Herein, a simple and efficient method for the palladium-catalyzed carbonylation of aryl boronic acids with unactivated alkyl iodides and bromides under visible-light irradiation, ambient temperature and low CO-pressure is presented. Notably, the procedure uses readily available equipment and an inexpensive palladium catalyst to generate the key alkyl radical intermediate. These mild conditions enabled the synthesis of a range of functionalized aryl alkyl ketones including the antipsychotic drug, melperone.
Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis
Zhang, Xiaheng,MacMillan, David W. C.
supporting information, p. 11353 - 11356 (2017/08/30)
A mechanism that enables direct aldehyde C-H functionalization has been achieved via the synergistic merger of photoredox, nickel, and hydrogen atom transfer catalysis. This mild, operationally simple protocol transforms a wide variety of commercially available aldehydes, along with aryl or alkyl bromides, into the corresponding ketones in excellent yield. This C-H abstraction coupling technology has been successfully applied to the expedient synthesis of the medicinal agent haloperidol.
Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides
Zhu, Xiaotao,Ye, Changqing,Li, Yajun,Bao, Hongli
supporting information, p. 10254 - 10258 (2017/08/07)
An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C?C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed.
A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations
Loman, Jacob. J.,Carnaghan, Emma R.,Hamlin, Trevor A.,Ovian, John M.,Kelly, Christopher B.,Mercadante, Michael A.,Leadbeater, Nicholas E.
, p. 3883 - 3888 (2016/05/24)
The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.
Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols
Huang, Feng-Qing,Xie, Jian,Sun, Jian-Guo,Wang, Yue-Wei,Dong, Xin,Qi, Lian-Wen,Zhang, Bo
supporting information, p. 684 - 687 (2016/03/01)
A novel and regioselective approach to carbonyl-containing alkyl chlorides via silver-catalyzed ring-opening chlorination of cycloalkanols is reported. Concurrent C(sp3)-C(sp3) bond cleavage and C(sp3)-Cl bond formation efficiently occur with good yields under mild conditions, and the chlorinated products are readily transformed into other useful synthetic intermediates and drugs. The reaction features complete regioselectivity, high efficiency, and excellent practicality. (Chemical Equation Presented).
Bimetallic nanosized solids with acid and redox properties for catalytic activation of C-C and C-H bonds
Cabrero-Antonino, Jose R.,Tejeda-Serrano, María,Quesada, Manuel,Vidal-Moya, Jose A.,Leyva-Pérez, Antonio,Corma, Avelino
, p. 689 - 696 (2016/12/28)
A new approach is presented to form self-supported bimetallic nanosized solids with acid and redox catalytic properties. They are water-, air- and H2-stable, and are able to activate demanding C-C and C-H reactions. A detailed mechanistic study on the formation of the Ag-Fe bimetallic system shows that a rapid redox-coupled sequence between Ag+, O2 (air) and Fe2+ occurs, giving monodisperse Ag nanoparticles supported by O-bridged diatomic Fe3+ triflimides. The system can be expanded to Ag nanoparticles embedded within a matrix of Cu2+, Bi3+ and Yb3+ triflimide.
