69491-47-0Relevant academic research and scientific papers
Selective Synthesis of Substituted Pyridines and Pyrimidines through Cascade Annulation of Isopropene Derivatives
Chen, Lu,He, Runfa,Huang, Yubing,Li, Jiaming,Li, Jian,Li, Yibiao,Liu, Jiasheng,Liu, Yang
, p. 1620 - 1625 (2022/03/14)
Diverse substituted pyridines and pyrimidines with high selectivity were obtained using a concise and efficient protocol developed herein. The reaction proceeds via metal-free cascade annulation of isopropene derivatives. Using isopropene derivatives as C3 synthons, NH4I as the “N” source, and formaldehyde or dimethyl sulfoxide as the carbon source, this reaction realizes the efficient formation of intermolecular C-N and C-C bonds.
Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls
Blakemore, David C.,Cervantes-Reyes, Alejandro,Chinigo, Gary M.,Smith, Aaron C.,Szostak, Michal
supporting information, p. 1678 - 1683 (2022/03/14)
Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report a direct synthesis of diverse nitrogen-containing heteroaromatic biaryls by Pd-catalyzed decarbonylative Suzuki cross-coupling of widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature of this cross-coupling enabled the straightforward preparation of >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, and quinolines in excellent yields. We anticipate that the modular nature of this protocol will find broad application in medicinal chemistry and drug discovery research.
Synthesis of Enaminone-Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki-Miyaura Cross Coupling Reaction
Fu, Leiqing,Cao, Xiaoji,Wan, Jie-Ping,Liu, Yunyun
, p. 254 - 258 (2020/01/25)
A series of Pd(II)-enaminone complexes, termed Pd(eao)2, have been synthesized and characterized. The investigation on the catalytic activities of these new Pd(II)-reagents has proved that the Pd(eao)2-1 possesses excellent catalytic activity for the Suzuki- Miyaura cross coupling reactions of aryl bromides/chlorides with aryl/vinyl boronic acids in the environmentally benign media of aqueous PEG400 at low loading (5 mol‰). The superiority of this Pd(II)-reagent to those commercial Pd(II) and Pd(0) catalysts in catalyzing the reactions has been confirmed by parallel experiments. What's more, Pd(eao)2-2 has been found as a practical catalyst for the homo-coupling reactions of aryl boronic acids.
Method for preparing biaryl from aryl hydrazine and aryl bromide
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Paragraph 0040; 0041; 0042; 0044, (2018/09/21)
The invention discloses a method for preparing biaryl from aryl hydrazine and aryl bromide. The method comprises the following steps: under the action of a divalent palladium catalyst and a ligand, aryl hydrazine and aryl bromide are subjected to a denitrification coupling reaction in an organic solvent, and after the reaction is ended, the reaction product is subjected to aftertreatment to obtainthe biaryl. In the preparation method, cheap and easily available aryl bromide is used as an aryl source, and the reaction of aryl hydrazine and aryl bromide shows good functional group tolerance, and promotes the palladium catalytic process by alkali.
Nitro group reduction and Suzuki reaction catalysed by palladium supported on magnetic nanoparticles modified with carbon quantum dots generated from glycerol and urea
Gholinejad, Mohammad,Zareh, Fatemeh,Nájera, Carmen
, (2017/09/06)
Glycerol and urea were used as green and cheap sources of carbon quantum dots (CQD) for modifying Fe3O4 nanoparticles (NPs). The obtained CQD@Fe3O4 NPs were used for the stabilization of palladium species and the prepared catalyst, Pd@CQD@Fe3O4, was characterized using various techniques. This magnetic supported palladium was applied as an efficient catalyst for the reduction of aromatic nitro compounds to primary amines at room temperature using very low palladium loading (0.008?mol%) and also for the Suzuki–Miyaura cross-coupling reaction of aryl halides as well as challenging heteroaryl bromides and aryl diazonium salts with arylboronic acids and with potassium phenyltrifluoroborate. This magnetically recyclable catalyst was recovered and reused for seven consecutive runs in the reduction of 4-nitrotoluene to p-toluidine and for ten consecutive runs in the reaction of 4-iodoanisole with phenylboronic acid with small decrease of activity. The catalyst reused in the Suzuki reaction was characterized using transmission electron microscopy, vibrating sample magnetometry and X-ray photoelectron spectroscopy. Using experiments such as hot filtration and poisoning tests, it has been shown that the true catalyst works under homogeneous conditions according to the release–return pathway of active palladium species.
Denitrogenative palladium-catalyzed coupling of aryl halides with arylhydrazines under mild conditions
Chang, Sheng,Dong, Lin Lin,Song, Hai Qing,Feng, Bo
supporting information, p. 3282 - 3288 (2018/05/15)
The development of a method for the Pd(ii)-catalyzed denitrogenative coupling of arylhydrazines to give functionalized biaryls in good yield, using aryl bromides or aryl iodides as convenient and inexpensive aryl sources, is reported. High functional group tolerance is demonstrated for electronically distinct arylhydrazines as well as aryl halides. The desired products were isolated in good to excellent yields for 58 examples. Control experiments and mechanism studies revealed that the transformation undergoes a base-promoted Pd-catalyzed process.
An immobilized symmetrical bis-(NHC) palladium complex as a highly efficient and recyclable Suzuki-Miyaura catalyst in aerobic aqueous media
Begum, Tahshina,Mondal, Manoj,Borpuzari, Manash Protim,Kar, Rahul,Kalita, Golap,Gogoi, Pradip K.,Bora, Utpal
supporting information, p. 539 - 546 (2017/01/10)
A bis-N-heterocyclic carbene (NHC) functionalized with chloropropyltriethoxysilane over silica was used to synthesize a well-defined immobilized palladium complex. This complex is a suitable and easily retrievable catalyst for Suzuki-Miyaura cross-coupling reactions under mild aqueous conditions. Excellent yields and conversions were obtained with low palladium loadings (down to 0.03 mol% Pd). The catalyst can be reused up to six cycles without the loss of its activity. The catalytic role of the NHC complex of palladium during coupling between bromobenzene and phenylboronic acid was investigated theoretically. The oxidative addition step is predicted to be endothermic in agreement with the experimental conditions.
Insight into Copper Catalysis: In Situ Formed Nano Cu2O in Suzuki-Miyaura Cross-Coupling of Aryl/Indolyl Boronates
Ranjani, Ganapathy,Nagarajan, Rajagopal
, p. 3974 - 3977 (2017/08/14)
A ligand-free copper catalyzed Suzuki-Miyaura coupling of 3,5-diiodopyridine with aryl and indole boronates has been explored in good to excellent yields. In situ generation of nano-Cu2O from CuCl2 under the reaction conditions has been discovered for the first time. The generality of the reaction was further demonstrated by the arylation of 5-iodopyrimidine, iodopyridines, iodobenzenes, and diiodobenzenes and resulted in good to moderate yields. Moreover, bisindole alkaloid Scalaridine A has been successfully synthesized in 60% overall yield.
Suzuki–Miyaura Cross-Coupling in Aqueous Medium Using Recyclable Palladium/Amide-Silica Catalyst
Mondal, Manoj,Dewan, Anindita,Begum, Tahshina,Gogoi, Pradip K.,Thakur, Ashim Jyoti,Bora, Utpal
, p. 1718 - 1728 (2016/08/30)
Abstract: Silica-immobilized benzamide palladium complex was prepared and characterized. The complex exhibits excellent catalytic activity and stability for Suzuki–Miyaura cross-coupling reaction under mild aqueous reaction condition. Various aryl bromide
Metal-free arylation of pyrimidines through a photochemical process
Ruch, Jonas,Aubin, Ariane,Erbland, Guillaume,Fortunato, Audrey,Goddard, Jean-Philippe
supporting information, p. 2326 - 2329 (2016/02/18)
Pyrimidinyl and pyrazinyl radicals were generated under moderate energetic irradiation conditions (UVA), and proved to be prompt to undergo C-C bond formation processes. Hetero-biaryl derivatives were obtained in good to high yields with highly interesting functional group selectivities. Bis hetero-biaryls were also easily accessible leading to original compounds, ready for further transformations. Experiments supporting radical processes have been reported.
