82525-17-5Relevant articles and documents
Insight into Copper Catalysis: In Situ Formed Nano Cu2O in Suzuki-Miyaura Cross-Coupling of Aryl/Indolyl Boronates
Ranjani, Ganapathy,Nagarajan, Rajagopal
supporting information, 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.
Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water
Ramakrishna,Dastagiri Reddy
, p. 8598 - 8610 (2017/07/12)
N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.
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.
A fast and oxygen-promoted protocol for the ligand-free Suzuki reaction of 2-halogenated pyridines in aqueous media
Liu, Chun,Yang, Weibo
supporting information; experimental part, p. 6267 - 6269 (2010/02/16)
A fast protocol has been developed for the construction of 2-aryl-substituted pyridine derivatives by the oxygen-promoted, ligand-free, Pd(OAc)2-catalyzed Suzuki reaction of 2-halogenated pyridines in aqueous isopropanol.
Structural studies on bioactive compounds. Part 37. Suzuki coupling of diaminopyrimidines: A new synthesis of the antimalarial drug pyrimethamine
Richardson, Marianne L.,Stevens, Malcolm F.G.
, p. 482 - 484 (2007/10/03)
Suzuki reactions have been used successfully to effect cross-coupling of 5-halopyrimidines with 4-chlorobenzeneboronic acid and 2,4-diamino-5-(4-chloro-3-halo)-6-ethylpyrimidines with 4-methoxybenzeneboronic acid. The antimalarial drug pyrimethamine has been prepared by coupling 2,4-diamino-6-ethyl-5-iodopyrimidine with 4-chlorobenzeneboronic acid.
Bridged Hydroquinolines
Balasubrahmanyam, S. N.,Jeyashri, B.
, p. 559 - 562 (2007/10/02)
The pyridannulation procedure of condensing vinamidinium salts with ketones having a free α-methylene has been adapted to prepare 3-substituted 5,6,7,8-tetrahydroquinolines; characterization data for the seven systems synthesized are reported.Conditions required are less drastic than those for recently reported alternative approaches to analogous systems.The adaption has considerable generality even though 5,8-methano-bridged 5,6,7,8-tetrahydroquinolines are not accessible through it.Chirality in the starting ketone, not affected by exposure to enolizing conditions, is preserved in the pyridannulated products.
A NEW AND FACILE SYNTHESIS OF 5-ARYLPYRIMIDINES AND 4-ARYLPYRAZOLES
Kano, Shinzo,Yuasa, Yoko,Shibuya, Shiroshi,Hibino, Satoshi
, p. 1079 - 1082 (2007/10/02)
A condensation of 2-aryl-3-(methylthio)acroleins (3a)-(3e), a new masked form of arylmalondialdehydes, with amidines yielded the corresponding 5-arylpyrimidines (4a)-(4k).Similarly, the reaction of 3 with N-substituted hydrazines gave the corresponding 1-
