101-54-2Relevant articles and documents
Synthesis and properties of 4-[(E)-(4'-R-phenyl)diazenyl]phthalonitriles and cobalt phthalocyanines obtained therefrom
Tikhomirova,Gruzdeva,Shaposhnikov
, p. 2778 - 2785 (2015)
The diazotization-azocoupling method has been utilized to prepare a series of previously unknown 4-[(E)-(4'-R-phenyl)diazenyl]phthalonitriles, which were further transformed into the corresponding cobalt phthalocyanines. The effect of the peripheral substitution of the phthalocyanine ligand on the spectral properties of the prepared compounds has been demonstrated.
Preparation of N-phenyl-p-phenylenediamine by coupling of aniline and nitrobenzene in KOH–poly(ethylene glycol) medium
Babkin, Alexander V.,Asachenko, Andrey F.,Uborsky, Dmitry V.,Kononovich, Dmitry S.,Izmer, Vyatcheslav V.,Kudakina, Vera A.,Shnaider, Viktoriya A.,Shevchenko, Nikolay E.,Voskoboynikov, Alexander Z.
, p. 555 - 557 (2016)
A novel protocol for efficient coupling of nitrobenzene and aniline in poly(ethylene glycol) medium in the presence of KOH giving diphenylamine derivatives has been developed, to enable the exclusion of the toxic tetramethylammonium hydroxide catalyst commonly used in the rubber antidegradant industry.
2,6-Bis(diphenylphosphino)pyridine: A simple ligand showing high performance in palladium-catalyzed CN coupling reactions
Nadri, Shirin,Rafiee, Ezzat,Jamali, Sirous,Joshaghani, Mohammad
, p. 4098 - 4101 (2014)
The use of commercially available 2,6-bis(diphenylphosphino)pyridine as a ligand in conjunction with K2CO3, DMAc and TBAB is an effective method for the palladium-catalyzed CN coupling of a variety of aryl halides with anilines, N-heterocyclic aromatic amines, and a cyclic secondary amine. The reactions proceed in good to excellent yield (up to 98%) while the loading of Pd(OAc)2 was as low as 0.025 mol %.
Gold(I)-mediated rearrangement of 1,2-diphenylhydrazine to semidines
Xia, Aibing,James, Alan J.,Sharp, Paul R.
, p. 451 - 453 (1999)
Reaction of 1,2-diphenylhydrazine with the gold oxo complex [(PPh3Au)3(μ-O)]BF4 gives a mixture of [(Ph3PAu)3(μ-N-1,4-C6H 4-NHPh)]BF4 (1; 82%) and [(Ph3PAu)3(μ-N-1,2-C6H 4-NHPh)]BF4 (2; 18%) in CH2-Cl2 at ambient temperature, A crossover experiment using a 1:1 mixture of 1,2-diphenylhydrazine and 1,2-diphenylhydrazine-d10 indicates that the rearrangement process is intramolecular.
Heterogeneous Catalytic Transfer Hydrogenation of 4-Nitrodiphenylamine to p-Phenylenediamines
Banerjee, Ankur A.,Mukesh, Doble
, p. 1275 - 1276 (1988)
p-Phenylenediamine analogues have been prepared from 4-nitrodophenylamine (1) by catalytic transfer hydrogenation in one stage; the process can be extended to the general condensation of a nitro compound with an alcohol (with Raney nickel as catalyst) or a ketone (with palladium as catalyst).
EPR and pulsed ENDOR study of intermediates from reactions of aromatic azides with group 13 metal trichlorides
Bencivenni, Giorgio,Cesari, Riccardo,Nanni, Daniele,El Mkam, Hassane,Walton, John C.
, p. 713 - 725 (2010)
The reactions of group 13 metal trichlorides with aromatic azides were examined by CW EPR and pulsed ENDOR spectroscopies. Complex EPR spectra were obtained from reactions of aluminium, gallium and indium trichlorides with phenyl azides containing a variety of substituents. Analysis of the spectra showed that 4-methoxy-, 3-methoxy- and 2-methoxyphenyl azides all gave 'dimer' radical cations [ArNHC6H4NH2]+ and trimers [ArNHC6H4NHC6H4NH 2]+ followed by polymers. 4-Azidobenzonitrile, with its electron-withdrawing substituent, did not react. In general the aromatic azides appeared to react most rapidly with AlCl3 but this reagent tended to generate much polymer. InCl3 was the least reactive group 13 halide. DFT computations of the radical cations provided corroborating evidence and suggested that the unpaired electrons were accommodated in extensive π-delocalised orbitals. A mechanism to account for the reductive conversion of aromatic azides to the corresponding anilines and thence to the dimers and trimers is proposed.
Nickel(0)/N-heterocyclic carbene complexes catalysed arylation of aromatic diamines
Kuhl, Sébastien,Fort, Yves,Schneider, Rapha?l
, p. 6169 - 6177 (2005)
Nickel complexes of N-heterocyclic carbenes were examined for effecting C-N coupling reactions between aromatic diamines and aryl chlorides of varying electron density. The Ni(0) ? 2IPr (IPr = N,N′-bis(2,6- diisopropylphenyl)imidazol-2-ylidene) complex associated to t-BuONa allowed N,N′-diarylation at 100 °C in 1,4-dioxane with excellent yields. Selective monoarylation of diamines could be performed in THF at 65 °C.
CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
Mohammadinezhad, Arezou,Akhlaghinia, Batool
, p. 15525 - 15538 (2019)
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water
Venkateswarlu, Katta,Rao, Kanusu Umamaheswara
, (2021/03/03)
The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.
Para -Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway
Viveki, Amol B.,Garad, Dnyaneshwar N.,Gonnade, Rajesh G.,Mhaske, Santosh B.
, p. 1565 - 1568 (2020/02/13)
Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp2)-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.
