25753-84-8

Usage

Reaction

Copper-catalyzed coupling of imidazoles and pyrazoles with 1,1-dibromo-1-alkenes: a distinct approach for direct Nalkynylation of heteroarenes. Synthesis of benzoindoloquinolizines via a Cu(I)-mediated C-N bond formation. Efficient synthesis of 1,4-disubstituted triazolyl N-carboxamides via a simple and convenient MCR using basic alumina as a solid support. Cu(I) complexes with diethoxyphosphoryl-1,10-phenanthrolines in catalysis of C-C and C-heteroatom bond formation.

Upstream product

• 114487-18-2 {(1,10-phenanthroline)2Cu}(formate) 
• 292850-64-7 {(1,10-phenanthroline)2Cu}{B(C₆H₅)4} 
• 80711-23-5 (1,10-phenanthroline)(triphenylphosphine)Cu(tetrahydroborate) 
• 114632-08-5 (1,10-phenanthroline)2Cu(tetrahydroborate) 
• 66-71-7 1,10-Phenanthroline 
• 100-39-0 benzyl bromide 
• 15709-74-7 bromotris(triphenylphosphine)copper(I) 
• 32474-61-6 (1,10-phenanthroline)(triphenylphosphine)Cu(formate) 

Downstream Products

• 114487-22-8 {(1,10-phenanthroline)(CyNC)2Cu}{BPh₄} 
• 32474-61-6 (1,10-phenanthroline)(triphenylphosphine)Cu(formate) 
• 71504-71-7 (1,10-phenanthroline)(triphenylphosphine)Cu(O-methyl-dithiocarbonate) 
• 114502-36-2 (1,10-phenanthroline)(triphenylphosphine)Cu(bicarbonate) 
• 114487-21-7 {(1,10-phenanthroline)(CyNC)2Cu}(bicarbonate) 
• 64666-62-2 (triphenylphosphine)2Cu(O-methyl-dithiocarbonate) 

Relevant academic research and scientific papers

Structural and electrochemical studies of copper(I) complexes with diethoxyphosphoryl-1,10-phenanthrolines

Two series of copper(I) complexes with diethoxyphosphoryl-substituted 1,10-phenanthroline ligands were synthesized and characterized in the solid state and in solution. The first comprised mixed-ligand CuI complexes with phenanthroline and triphenylphosphine. The second series includes bis-chelates with two phenanthroline ligands. According to the X-ray data for the six complexes, the ditopic phenanthroline ligands exhibit bidentate coordination to the copper(I) atom through two nitrogen atoms in both series. Solution equilibria involving different phenanthroline copper(I) species were studied by 1H and 31P NMR spectroscopy, electrochemistry, and spectroelectrochemistry. The solution speciation of these labile complexes is different for these two series and depends on the nature of solvent and the location of the phosphorus substituent on the phenanthroline backbone. Coordinating solvents can replace a bromide, triphenylphosphine, and even a phenanthroline ligand in the inner coordination sphere of the metal center. Copper(I) complexes with α-substituted phenanthrolines easily dissociate even in noncoordinating solvents such as CH2Cl2 and CHCl3. Ligand-exchange reactions leading to less sterically hindered species were observed under the utilized solution conditions. The coordination mode of the phenanthroline chelators does not change under any of the utilized solution conditions, and binding of the phosphoryl group to the metal center was never observed by spectroscopic or spectroelectrochemical methods. Copper(I) complexes with diethoxyphosphoryl-substituted 1,10-phenanthroline ligands are synthesized and characterized in the solid state and in solution by X-ray diffraction, 1H and 31P NMR spectroscopy, electrochemistry, and spectroelectrochemistry. Copyright

Synthesis, structures, DNA-binding and anticancer activities of some copper(I)-phosphine complexes

Copper(I) complexes with a phenanthroline-phosphine set of ligands were synthesized by refluxing methanolic solutions of CuBr2 with at least a four fold molar excess of the phosphine ligands, followed by the treatment of the formed {CuBr(PR3)3 complexes [R = phenyl (1a), 4-fluorophenyl (1b), cyclohexyl (1c) or 4-methoxyphenyl (1d)]} with 1 molar equivalent of 1,10-phenanthroline in DCM. The tris(4-methoxyphenyl)phosphine ligand afforded the complex [Cu(P[C6H4-4-OMe]3)2(phen)]Br (2d), while the other phosphines produced complexes with the general formula CuBr(PR3)(phen) [R = phenyl (2a), 4-fluorophenyl (2b) or cyclohexyl (2c)]. The new complexes were characterized by elemental analysis, 31P NMR spectroscopy and mass spectrometry. Additional confirmation of the structures of 1b, 2b, 2c and 2d were determined by single crystal X-ray diffraction. A DNA-binding study of the complexes 2a–2d against ct-DNA showed binding constant values that correspond to the intercalation mode of binding. The notable variations in the binding constants of the complexes suggest some contribution from the phosphine ligands. The lipophilicity of the complexes was evaluated theoretically and the calculated log P value of complex 2d is positive and high, being in the same range of relatively easy membrane penetrating drugs. The calculated log P values of complexes 2a–2c are negative, indicating a low membrane permeability. Complexes 2a–2d were examined against four different cancer cell lines. The choice of the phosphine ligand appears to influence the copper(I)-phosphine anticancer activities against the different cancer cell lines. The data suggested that complexes 2a and 2d show potential anticancer activity against prostate and breast cancers. The four copper complexes were docked against four different proteins associated with prostate or breast cancers activities, highlighting some of the structural-DNA interactions.

Structural and electrochemical studies of copper(I) complexes with diethoxyphosphoryl-1,10-phenanthrolines

Two series of copper(I) complexes with diethoxyphosphoryl-substituted 1,10-phenanthroline ligands were synthesized and characterized in the solid state and in solution. The first comprised mixed-ligand CuI complexes with phenanthroline and triphenylphosphine. The second series includes bis-chelates with two phenanthroline ligands. According to the X-ray data for the six complexes, the ditopic phenanthroline ligands exhibit bidentate coordination to the copper(I) atom through two nitrogen atoms in both series. Solution equilibria involving different phenanthroline copper(I) species were studied by 1H and 31P NMR spectroscopy, electrochemistry, and spectroelectrochemistry. The solution speciation of these labile complexes is different for these two series and depends on the nature of solvent and the location of the phosphorus substituent on the phenanthroline backbone. Coordinating solvents can replace a bromide, triphenylphosphine, and even a phenanthroline ligand in the inner coordination sphere of the metal center. Copper(I) complexes with α-substituted phenanthrolines easily dissociate even in noncoordinating solvents such as CH2Cl2 and CHCl3. Ligand-exchange reactions leading to less sterically hindered species were observed under the utilized solution conditions. The coordination mode of the phenanthroline chelators does not change under any of the utilized solution conditions, and binding of the phosphoryl group to the metal center was never observed by spectroscopic or spectroelectrochemical methods. Copper(I) complexes with diethoxyphosphoryl-substituted 1,10-phenanthroline ligands are synthesized and characterized in the solid state and in solution by X-ray diffraction, 1H and 31P NMR spectroscopy, electrochemistry, and spectroelectrochemistry.

Methods and systems for preparing fused heterocyclic compounds using copper(I) catalysts

A copper(I)-catalyzed procedure for the synthesis of benzo[b]heterocycles. This protocol can be used to synthesize a variety of 2-arylbenzo[b]furans and indoles in good to excellent yields. This method can tolerate a variety of functional groups, does not require the use of expensive additives and is palladium-free.

Methods of 1,3-enyne preparation using copper (I) catalysts

A copper(I) bi-dentate ligand complex-catalyzed procedure for synthesis of 1,3-enynes. The methods and/or systems of this invention afford a variety of enynes, tolerate a variety of sensitive functional groups, and can be employed without resort to expensive palladium reagents.