14674-99-8Relevant academic research and scientific papers
A facile and rapid route for the synthesis of Cu/Cu2O nanoparticles and their application in the Sonogashira coupling reaction of acyl chlorides with terminal alkynes
Bhosale, Manohar A.,Sasaki, Takehiko,Bhanage, Bhalchandra M.
, p. 4274 - 4280 (2014)
We have demonstrated a facile one-step synthetic strategy for the preparation of Cu/Cu2O nanoparticles (NPs) via a microwave method. The microwave energy acts as a driving force for the synthesis of Cu/Cu2O NPs, which makes the proce
Flexible Construction of Functionalized-Pyrroles under Palladium or Copper Catalysis in the Presence of BF3 ? Et2O
Liu, Yin,Liu, Teng,Yan, Biwei,Wei, Kun,Guo, Wusheng
, p. 916 - 921 (2022/01/26)
We have developed a flexible approach enabling the access to highly functionalized pyrroles under palladium or copper catalysis in the presence of BF3 ? Et2O. This catalytic methodology utilizes commercially available amines as react
One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source
Xiong, Wenfang,Wu, Bowen,Zhu, Baiyao,Tan, Xiaobin,Wang, Lu,Wu, Wanqing,Qi, Chaorong,Jiang, Huanfeng
, p. 2843 - 2851 (2021/05/10)
Carbonylation coupling reaction has emerged as a powerful and versatile strategy for the construction of carbonyl-containing compounds in modern synthetic chemistry over the past years. Carbon dioxide, a renewable one carbon molecule, has become one of the most attractive and promising alternative carbonyl sources due to its highly abundance, nontoxicity and stability in comparison with CO in recent years. However, in most cases, a two-chamber technique was generally necessary to allow the CO-producing and CO-consuming processes to perform successfully because of the complexities and incompatibility of reaction conditions, when carbon dioxide was utilized as carbonyl source. Herein, a practical one-pot protocol using carbon dioxide as the carbonyl source for the palladium-catalyzed carbonylative Sonogashira coupling has been established, providing an expedient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions. By finding a suitable catalytic system, the method allowed the CO-generating and CO-consuming processes to proceed in one pot, wherein carbon monoxide was generated in situ from the reduction of carbon dioxide in the absence of any fluoride reagents. Simple and safe operation, readily available substrates, good functional group tolerance and mild reaction conditions are the features of the method.
Synthesis of Isoselenazoles and Isothiazoles from Demethoxylative Cycloaddition of Alkynyl Oxime Ethers
Zhang, Zhu-Zhu,Chen, Rong,Zhang, Xiao-Hong,Zhang, Xing-Guo
, p. 632 - 642 (2020/12/22)
A general method for the synthesis of isoselenazoles and isothiazoles has been developed by the base-promoted demethoxylative cycloaddition of alkynyl oxime ethers using the cheap and inactive Se powder and Na2S as selenium and sulfur sources. This transformation features the direct construction of N-, Se-, and S-containing heterocycles through the formation of N-Se/S and C-Se/S bonds in one-pot reactions with excellent functional group tolerance.
Base-Promoted Synthesis of Polysubstituted 4-Aminoquinolines from Ynones and 2-Aminobenzonitriles under Transition-Metal-Free Conditions
Kumar, Ankit,Mishra, Pawan K.,Saini, Kapil Mohan,Verma, Akhilesh K.
supporting information, p. 2546 - 2551 (2021/03/16)
A transition-metal-free and base-promoted one-pot reaction of ynones with 2-aminobenzonitriles is described. The reaction was initiated through sequential aza-Michael addition/intramolecular annulation to afford various multisubstituted 4-aminoquinolines
Synthesis of 2-isoxazolyl-2,3-dihydrobenzofuransviapalladium-catalyzed cascade cyclization of alkenyl ethers
Zhou, Fei,Li, Can,Li, Meng,Jin, Yangbin,Jiang, Huanfeng,Zhang, Yingjun,Wu, Wanqing
supporting information, p. 4799 - 4802 (2021/05/25)
A novel palladium-catalyzed cascade cyclization reaction of alkenyl ethers with alkynyl oxime ethers for the construction of poly-heterocyclic scaffolds has been developed, in which the electron-rich alkene moiety functions as a three-atom unit, simultaneously dealing well with the coordination and regioselectivity of electron-rich olefins under metal catalysis. The strategy features excellent regio- and chemoselectivities as well as good functional group tolerance. Moreover, the newly formed 2-isoxazolyl-2,3-dihydrobenzofuran products can be further transformed to diverse complex heterocycles, demonstrating their potential applications in organic synthesis and medicinal chemistry.
Methylation Alkynylation of Terminal Alkenes via 1,2-Alkynyl Migration Using Dicumyl Peroxide as the Methyl Source
Qin, Yi-Qun,Chen, De,Liu, Liang,Zhang, Jia-Jia,Peng, Xin-Ju,Luo, Yong-Yue,Deng, Wei,Xiang, Jiannan
, p. 4700 - 4708 (2021/08/31)
The metal-free oxidative alkene methylation/alkynylation of 1,4-enyn-3-ols with an organic peroxide as the methyl source has been developed, which provides straightforward and practical access to the challenging quaternary-carbon-containing but-3-yn-1-one
Electrochemical Palladium-Catalyzed Oxidative Sonogashira Carbonylation of Arylhydrazines and Alkynes to Ynones
Cao, Yue,Hu, Jingcheng,Lei, Aiwen,Li, Haoran,Shi, Renyi,Wu, Yong,Xu, Minghao,Yi, Hong,Zeng, Li
supporting information, p. 12460 - 12466 (2021/08/24)
Oxidative carbonylation using carbon monoxide has evolved as an attractive tool to valuable carbonyl-containing compounds, while mixing CO with a stoichiometric amount of a chemical oxidant especially oxygen is hazardous and limits its application in scale-up synthesis. By employing anodic oxidation, we developed an electrochemical palladium-catalyzed oxidative carbonylation of arylhydrazines with alkynes, which is regarded as an alternative supplement of the carbonylative Sonogashira reaction. Combining an undivided cell with constant current mode, oxygen-free conditions avoids the explosion hazard of CO. A diversity of ynones are efficiently obtained using accessible arylhydrazines and alkynes under copper-free conditions. A possible mechanism of the electrochemical Pd(0)/Pd(II) cycle is rationalized based upon cyclic voltammetry, kinetic studies, and intermediates experiments.
Recyclable heterogeneous palladium-catalyzed carbonylative Sonogashira coupling under CO gas-free conditions
Zhou, Zebiao,Li, Jianying,Xu, Zhaotao,Cai, Mingzhong
supporting information, p. 2015 - 2025 (2020/05/13)
A convenient, efficient and practical heterogeneous palladium-catalyzed carbonylative Sonogashira coupling of aryl iodides with terminal alkynes under CO gas-free conditions has been developed by using an MCM-41-supported bidentate phosphine palladium ace
Visible-light-mediated photocatalytic cross-coupling of acetenyl ketones with benzyl trifluoroborate
Zhang, Lingchun,Chu, Yanle,Ma, Peizhi,Zhao, Shujuan,Li, Qiaoyan,Chen, Boya,Hong, Xuejiao,Sun, Jun
supporting information, p. 1073 - 1077 (2020/02/22)
In this report, we describe a simple visible light-triggered Barbier-type reaction by employing acetenyl ketones with benzyl trifluoroborates. Through a radical-radical cross-coupling process, this photocatalytic protocol furnished a wide range of tertiary propargyl alcohols. Mechanistic investigation indicated that proton-coupled electron transfer (PCET) might be involved in the photochemical transformations.
