124857-13-2Relevant academic research and scientific papers
Heterogeneous metallo-organocatalysis for the selective one-pot synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone
Genelot, Marie,Dufaud, Véronique,Djakovitch, Laurent
, p. 976 - 981 (2011)
One-pot tandem heterogeneously catalyzed procedures for the selective synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone have been developed. For this purpose, heterogeneous palladium-, amine-, and phosphine-catalysts were prepared by post-synthe
An Efficient Synthesis of (1-Methyl)-2-phenyl-4-quinolones from (N-Methyl)isatoic Anhydride
In Lee, Jae
supporting information, p. 556 - 558 (2021/02/09)
The acyl substitution of (N-methyl)isatoic anhydride with N,O-dimethylhydroxylamine hydrochloride in CH3CN gave N-methoxy-N-methyl 2-(N-methyl)aminobenzamide, which was treated with ethynyllithium reagents to afford 1-[2-(N-methyl)amino]-3-phen
Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source
Lyu, Xue,Sun, Guanglong,Zhou, Yang,Wang, Yingying,Lei, Min,Wu, Wanying,Guo, Dean
, p. 309 - 315 (2019/01/21)
Abstract: A practical and efficient palladium-catalyzed carbonylative Sonogashira cross-coupling reaction for the synthesis of alkynones from aryl iodides, alkynes, and formic acid as the CO source has been described. Under the assistance of PPh3/I2, formic acid can be used as the CO source for synthesis of alkynones in moderate–good yields. Furthermore, it is also successfully applied for the modification of natural products, such as vindoline and tabersonin, to obtain the corresponding products.
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 facile and efficient method for the synthesis of alkynone by carbonylative Sonogashira coupling using CHCl3 as the CO source
Sun, Guanglong,Lei, Min,Hu, Lihong
, p. 28442 - 28446 (2016/04/09)
A facile and efficient method for the synthesis of alkynones by a Pd-catalyzed carbonylative Sonogashira coupling reaction starting from aryl iodide, terminal alkyne and chloroform (CHCl3) as the CO source is described. This procedure proves th
Highly efficient synthesis of flavones: Via Pd/C-catalyzed cyclocarbonylation of 2-iodophenol with terminal acetylenes
Zhu, Fengxiang,Li, Yahui,Wang, Zechao,Wu, Xiao-Feng
, p. 2905 - 2909 (2016/05/24)
A highly efficient and selective Pd/C-catalyzed ligand-free cyclocarbonylation reaction for the synthesis of flavones has been developed. Various flavone derivatives were isolated in excellent yields with excellent functional group tolerances. Additionally, catalyst reuse experiments were performed successfully as well.
Synthesis of 4-quinolones via a carbonylative sonogashira cross-coupling using molybdenum hexacarbonyl as a co source
?kerbladh, Linda,Nordeman, Patrik,Wejdemar, Matyas,Odell, Luke R.,Larhed, Mats
, p. 1464 - 1471 (2015/02/19)
A palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence for the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes via two different protocols is described. The first method (A) yields the cyclized products
Gold-catalyzed conversion of aryl- and alkyl-substituted 1-(o-aminophenyl)-2-propyn-1-ones to the corresponding 2-substituted 4-quinolones
Seppaenen, Otto,Muuronen, Mikko,Helaja, Juho
, p. 4044 - 4052 (2014/07/08)
Gold-catalyzed cyclization of alkyl- or aryl-substituted 1-(o-aminophenyl)-2-propyn-1-ones to the corresponding 2-substituted 4-quinolones was studied with various gold salts and complexes. Screening of the different catalysts showed highest performance w
Recyclable and reusable PdCl2(PPh3) 2/PEG-2000/H2O system for the carbonylative Sonogashira coupling reaction of aryl iodides with alkynes
Zhao, Hong,Cheng, Mingzhu,Zhang, Jiatao,Cai, Mingzhong
supporting information, p. 2515 - 2522 (2014/05/06)
PdCl2(PPh3)2 in a mixture of water and poly(ethylene glycol) (PEG-2000) is shown to be an extremely active catalyst for the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes. The reaction can be conducted under an atmospheric pressure of carbon monoxide at 25 °C with Et3N as a base, yielding a variety of alkynyl ketones in good to excellent yields. Application of this synthetic method to prepare flavones from o-iodophenol and terminal alkynes was also achieved. The isolation of the products is readily achieved by extraction with diethyl ether, and the PdCl2(PPh3)2/PEG-2000/ H2O system can be easily recycled and reused six times without any loss of catalytic activity. the Partner Organisations 2014.
Aryl-palladium-NHC complex: Efficient phosphine-free catalyst precursors for the carbonylation of aryl iodides with amines or alkynes
Zhang, Chunyan,Liu, Jianhua,Xia, Chungu
supporting information, p. 9702 - 9706 (2015/02/19)
A series of aryl-palladium-NHC compounds was prepared according to the reported methods and their catalytic activity in the carbonylation of aryl iodides to synthesize α-keto amides and alkynones was examined. These practical aryl-palladium-NHC complexes have shown highly efficient catalyzed carbonylation and Sonogashira carbonylation reactions, with high turnover number in synthesis of α-keto amides (TON = 4300) and in synthesis of alkynones (TON = 980).
