412306-01-5Relevant academic research and scientific papers
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.
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.
A general two-step one-pot synthesis process of ynones from α-keto acids and 1-iodoalkynes
Zeng, Xiaobao,Liu, Chulong,Yang, Weiguang,Wang, Xingyong,Wang, Xinyan,Hu, Yuefei
supporting information, p. 9517 - 9520 (2018/08/28)
A general two-step one-pot synthesis process of ynones was developed by cycloaddition of α-keto acids and 1-iodoalkynes followed by a ring-opening reaction. Its easy conditions and novel mechanism endowed it with two distinctive advantages: iodine-atom bonded to C(sp2) remained intact and α-keto acids became a part of the triple bonds in ynones.
Rapid access to unsymmetrical tolanes and alkynones by sequentially palladium-catalyzed one-pot processes
G?tzinger, Alissa C.,Müller, Thomas. J. J.
, p. 3498 - 3500 (2016/04/19)
Alkynones as well as unsymmetrically substituted tolanes (diarylalkynes) can be rapidly generated in a one-pot fashion via sequential palladium catalysis. Terminal alkynes, formed in situ by protecting-group free palladium-catalyzed coupling of aryl iodides with ethynyl magnesium bromide, are subsequently transformed by Sonogashira coupling with aryl halides or aroyl chlorides to furnish unsymmetrically substituted alkynes in good to excellent yields.
One-pot three-component synthesis of pyrazoles through a tandem coupling-cyclocondensation sequence
Liu, Hai-Ling,Jiang, Huan-Feng,Zhang, Min,Yao, Wen-Juan,Zhu, Qiu-Hua,Tang, Zhou
, p. 3805 - 3809 (2008/09/21)
An efficient and general one-pot procedure for the synthesis of pyrazoles from acid chlorides, terminal alkynes and hydrazines was described via a coupling and cyclocondensation sequence. Acid chlorides coupled with terminal alkynes to give α,β-unsaturated ynones, and in situ converted into pyrazoles by the cycloaddition of hydrazines. The desired pyrazoles were obtained with 15-85% isolated yields.
