66737-07-3Relevant articles and documents
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.
Bifunctional Borane Catalysis of a Hydride Transfer/Enantioselective [2+2] Cycloaddition Cascade
Zhang, Ming,Wang, Xiao-Chen
supporting information, p. 17185 - 17190 (2021/07/06)
Herein, we present a mild and efficient method for synthesizing enantioenriched tetrahydroquinoline-fused cyclobutenes through a cascade reaction between 1,2-dihydroquinolines and alkynones with catalysis by chiral spiro-bicyclic bisboranes. The bisborane
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
Pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex and preparation and application thereof
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Paragraph 0109; 0110; 0111; 0112, (2019/06/11)
The invention relates to a pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex. The pyrene marked benzimidazole n-heterocyclic carbene palladium metal complex is prepared from benzimidazole serving as a skeleton and pyridine serving
Rhodium-Catalyzed Intermolecular trans-Disilylation of Alkynones with Unactivated Disilanes
He, Tao,Liu, Li-Chuan,Guo, Le,Li, Bin,Zhang, Qing-Wei,He, Wei
supporting information, p. 10868 - 10872 (2018/07/31)
Disilylation of alkynes could provide rapid entry to synthetically useful 1,2-bissilyl-alkenes, but is currently limited to activated disilanes reacting in an intramolecular fashion. Reported herein is an efficient rhodium(I)-catalyzed intermolecular disi
Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
Meng, Mengting,Wang, Guofang,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
, p. 1218 - 1231 (2018/02/16)
Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
Regio- and Stereoselective Hydrosulfonylation of Electron-Deficient Alkynes: Access to Both E- and Z-β-Sulfonyl-α,β-Unsaturated Carbonyl Compounds
Zhang, Wei,Johnson, Gabriel M.,Guan, Zhi,He, Yan-Hong
supporting information, p. 4562 - 4570 (2018/10/24)
A metal-free hydrosulfonylation of electron-deficient alkynes with sodium sulfinates or sulfinic acids to access both E- and Z-β-sulfonyl-α,β-unsaturated carbonyl compounds has been developed. We propose that this reaction via a hydroxylallene intermediate delivers the thermodynamically stable E isomer, or via a concerted termolecular AdE3 mechanism affords Z isomer. The stereoselectivity of addition (syn or anti) can be controlled by varying the sulfonyl sources and acidic buffer solutions. This protocol exhibits broad substrate scope for internal or terminal alkynes including various substituted ynones and alkynyl esters. This approach is mild, efficient, operationally simple and easy to be scaled-up. (Figure presented.).
Nickel catalysed carbonylative Sonogashira reaction for the synthesis of diarylalkynones and 2-substituted flavones
Charugandla, Renuka,Vangala, Markandeya Sarma,Chidara, Sridhar,Korupolu, Raghu Babu
supporting information, p. 3283 - 3287 (2018/07/25)
The nickel catalyzed, palladium/phosphine free carbonylative Sonogashira reaction of terminal alkynes with substituted aryl and heteroaryl iodides is described. This protocol provides mild and robust conditions to synthesize a variety of substituted aryl α,β-alkynyl ketones and flavones in good to excellent isolated yields. This methodology tolerates several functional groups such as electron donating (methyl, isopropyl, tert-butyl, methoxy) as well as electron withdrawing (trifluoromethyl, nitro, esters, nitrile) groups on the terminal alkynes and iodides.
A Convenient and Efficient Palladium-Catalyzed Carbonylative Sonogashira Transformation with Formic Acid as the CO Source
Peng, Jin-Bao,Wu, Fu-Peng,Li, Chong-Liang,Qi, Xinxin,Wu, Xiao-Feng
supporting information, p. 1434 - 1437 (2017/04/01)
A practical, convenient, and efficient palladium-catalyzed carbonylative Sonogashira reaction of aryl iodides was developed. With formic acid as the CO source and dicyclohexylcarbodiimide as the activator, various alkynones were produced in good to excell
