74448-90-1Relevant academic research and scientific papers
Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
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Page/Page column 109-110, (2020/01/09)
The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.
Magnetically retrievable nano crystalline nickel ferrite- catalyzed aerobic, ligand-free C-N, C-O and C-C cross-coupling reactions for the synthesis of a diversified library of heterocyclic molecules
Paul, Sanjay,Pradhan, Koyel,Ghosh, Sirshendu,De,Das, Asish R.
, p. 1301 - 1316 (2014/05/06)
A new nickel ferrite nano-crystal-catalyzed, ligand-free strategy for the construction of C-N, C-O, and C-C bonds is presented, in which easily available nitrogen and oxygen nucleophiles, aryl/heteroaryl halides and arylboronic acids are used for the cross-coupling reactions. The reactions can be performed at low catalyst loadings with excellent functional group tolerance and chemoselectivity. A variety of functional groups are compatible with the reaction conditions, including nitro, methoxy, as well as acid- and base-sensitive heteroaromatic groups. This unprecedented chemistry nicely complements classical methods for the N-arylation of amines/heteroamines, the O-arylation of phenols/hydroxycoumarins and biaryl/heteroaryl synthesis. The low cost, easy to handle nature and the simplicity of this catalytic system render the method competitive with comparable copper- and palladium-based protocols which require the presence of sophisticated ligands. Nickel ferrite magnetic nanoparticles were prepared by a simple hydrothermal method and characterized by using XRD, TEM image, energy dispersive X-ray analysis, XPS and FT-IR. The easy recovery of the catalyst and high yield of the products make the protocol attractive, sustainable and economic. The catalyst was reused for five cycles with almost unaltered catalytic activity.
Facile preparation of unsymmetrical diaryl ethers from unsymmetrical diaryliodonium tosylates and phenols with high regioselectivity
Kakinuma, Yohji,Moriyama, Katsuhiko,Togo, Hideo
, p. 183 - 188 (2013/02/23)
Unsymmetrical diaryl ethers were efficiently obtained in good yields by the reactions of aryl(4-methoxyphenyl)iodonium tosylates with phenols, and aryl(2,4-dimethoxyphenyl)iodonium tosylates with phenols, in the presence of potassium carbonate in acetonitrile, respectively. The latter iodonium tosylates provided the corresponding unsymmetrical diaryl ethers in good yields with high regioselectivities, together with the quantitative formation of 1-iodo-2,4-dimethoxybenzene. Georg Thieme Verlag Stuttgart New York.
Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system
Yang, Haitao,Xi, Chao,Miao, Zhiwei,Chen, Ruyu
supporting information; experimental part, p. 3353 - 3360 (2011/08/03)
The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.
Glyoxal bis(phenylhydrazone) as promoter for CuI-catalyzed O-arylation of phenols with bromoarenes
Liu, Yu-Hua,Li, Gang,Yang, Lian-Ming
experimental part, p. 343 - 346 (2009/04/19)
A very simple bishydrazone-type ligand, glyoxal bis(phenylhydrazone) (L1), was found to effectively promote the CuI-catalyzed O-arylation of phenols with aryl bromides. This cross-coupling reaction proceeded in acetonitrile at 60-80 °C in the presence of K3PO4 as base. A diverse array of phenols and bromoarenes was employed as substrates to afford diaryl ethers in good to excellent yields, and some base-sensitive groups, such as ester, aldehyde, and ketone groups, can survive under the mild reaction conditions.
Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols
Maiti, Debabrata,Buchwald, Stephen L.
supporting information; experimental part, p. 17423 - 17429 (2010/03/25)
O- or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates. We have developed a complementary set of Cu- and Pd-based catalyst systems for the selective O- and N-arylation of unprotected aminophenols using aryl halides. Selective O-arylation of 3- and 4-aminophenols is achieved with copper-catalyzed methods employing picolinic acid or CyDMEDA, trans-N,N′-dimethyl-1,2- cyclohexanediamine, respectively, as the ligand. The selective formation of N-arylated products of 3- and 4-aminophenols can be obtained with BrettPhos precatalyst, a biarylmonophosphine-based palladium catalyst. 2-Aminophenol can be selectively N-arylated with CuI, although no system for the selective O-arylation could be found. Coupling partners with diverse electronic properties and a variety of functional groups can be selectively transformed under these conditions.
Copper(I)-catalyzed C-C and C-O coupling reactions using hydrazone ligands
Mino, Takashi,Yagishita, Fumitoshi,Shibuya, Masanori,Kajiwara, Kenji,Shindo, Hiroaki,Sakamoto, Masami,Fujita, Tsutomu
experimental part, p. 2457 - 2460 (2010/01/07)
Copper-catalyzed C-C coupling reaction of aryl iodides with diethylmalonate in toluene at 90C gave arylated malonates using 5 mol% of CuI with hydrazone 1a as a ligand in good yields under an aerobic atmosphere. We also found CuI/hydrazone 1b in toluene to be an efficient catalytic system for C-O coupling reactions of aryl bromides with phenols to give aryl ethers in good yields at 110C under an aerobic atmosphere.
Synthesis of diaryl ethers through the copper-catalyzed arylation of phenols with aryl halides using microwave heating
He, Huan,Wu, Yong-Jin
, p. 3445 - 3446 (2007/10/03)
The copper-catalyzed arylation of phenols with a variety of aryl halides using microwave heating is described.
Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine
Evans, David A.,Katz, Jeffrey L.,West, Theodore R.
, p. 2937 - 2940 (2007/10/03)
Diaryl ethers are readily synthesized in high yield at room temperature through the copper(II)-promoted coupling of arylboronic acids and phenols. The reaction is tolerant of a wide range of substituents on both coupling partners. These reaction condition
