14192-97-3

Upstream product

• 1202-34-2 di(pyridin-2-yl)amine 
• 591-50-4 iodobenzene 
• 109-04-6 2-bromo-pyridine 
• 62-53-3 aniline 
• 109-09-1 2-chloropyridine 
• 6631-37-4 2-(phenylamino)pyridine 
• 108-86-1 bromobenzene 

Downstream Products

• 1262533-53-8 [Cu(N-phenyl-N,N-bis(2-pyridyl)amine)(Cl)(μ-Cl)]2 
• 1262533-75-4 [Cu(N-phenyl-N,N-bis(2-pyridyl)amine)(η2-styrene)][BF4]*(ethanol) 

Relevant academic research and scientific papers

A new reaction of N-aryl-2-pyrimidinamines with triphosgene

A new reaction of N-aryl-2-pyrimidinamines with triphosgene to afford N-aryl-N-(2-pyrimidinyl)-2-pyrimidinamine is described.

Kinetics and mechanistic study of polynuclear platinum(II) polypyridyl complexes; A paradigm shift in search of new anticancer agents

This paper reports on a mechanistic interaction between mononuclear and polynuclear platinum(II) complexes viz; phenyl-dichlorido-2,2′-dipyridinylaminediaquaplatinum(II) (PtC1); di-2-pyridylaminomethylbenzenediaquaplatinum(II) (PtC2); 1,3,5-tris(2,2′dipyr

Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes

A highly efficient solvent-free protocol for the Buchwald-Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded-ring N-heterocyclic carbene palladium complex (THP-Dipp)Pd(cinn)Cl [THP-Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene; cinn = cinnamyl, 3-phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents.

Evaluation of aromatic amination catalyzed by palladium on carbon: A practical synthesis of triarylamines

A heterogeneous palladium on carbon (Pd/C)-catalyzed coupling between amines and aromatic halides including aromatic chlorides has been achieved using sodium tert-butoxide (NaO-t-Bu) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand in cyclopentyl methyl ether (CPME). The use of potassium tert-butoxide (KO-t-Bu) in place of NaO-t-Bu brought about the benzyne-mediated aromatic amination even without Pd/C and dppf, giving a mixture of regioisomers when 4-substituted bromobenzenes were employed as the substrate. The combination of Pd/C, dppf, NaO-t-Bu could be utilized for the syntheses of a broad range of triarylamines by replacing CPME with mesitylene which can provide a higher reaction temperature. The Pd/C could be quantitatively recovered and reused until at least the fourth cycle without any loss in catalytic activity. The quite low leaching of palladium (1.1%) was demonstrated by an inductively coupled plasma-atomic emission spectrometric analysis.

NUCLEOPHILIC HETEROCYCLIC CARBENE DERIVATIVES OF PD(ACAC)2 FOR CROSS-COUPLING REACTIONS

Embodiments in accordance with the present invention provide for a palladium complex characterized by the general Formula (I): where A is a bidentate monoanionic ligand, NHC is a nucleophilic heterocyclic carbene, and Z is an anionic ligand. Such palladium complexes are useful in initiating cross-coupling reactions.

Synthesis of novel (NHC)Pd(acac)Cl complexes (acac=acetylacetonate) and their activity in cross-coupling reactions

The synthesis and characterization of two new complexes (IPr)Pd(acac) 2 (1) and (IPr)Pd(acac)Cl (2) (IPr=(N,N′-bis(2,6- diisopropylphenyl)imidazol)-2-ylidene, acac=acetylacetonate) are described. Complex 2 can be prepared in a one-pot protocol in high yield. A study detailing the versatility of 2 to effectively catalyze a series of cross-coupling reactions is discussed.

Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in N,N-Bis(2-pyridyl)amino-Substituted Arenes

The synthesis and X-ray crystal structures of two N,N-bis(2-pyridyl)amino (dpa)-substituted aromatic systems (Ar-dpa) 1 (Ar = 4,4′-disubstituted trans-stilbene) and 2 (Ar = 1,4-disubstituted benzene) and their ZnCl 2 complexes (1/ZnCl2 and 2/ZnCl2) are reported. The fluoroionophoric behavior of 1-2 in response to Zn(II) in acetonitrile also has been investigated. In addition, compound 3DPA has been prepared and served as a π-deconjugated model for 1DPA. The observed crystal structures for 1/ZnCl2 and 2/ZnCl2 could be divided into two distinct types, the planar and the twisted forms, depending on the aryl-dpa (Cph-NC3) dihedral angle. The twisted form is more favorable for these complexes unless the arene has a strong " push-pull" character. Nonetheless, the degree of π-conjugation between the N-pyridyl and the N-aryl group is reduced in both complex forms when compared with the free ligands. Such a Zn(II)-induced π-deconjugation not only directly affects the internal charge transfer (ICT) fluorescence of the dpa-substituted stilbenes but also facilitates the occurrence of photoinduced electron transfer (PET) from the stilbene donor to the dpa/Zn(II) acceptor. The PET process is particularly important in accounting for the observed Zn-(II)-induced fluorescence quenching for 1DPA as well as 3DPA.

The Problem of the Existence of C(Ar)-H...N Intramolecular Hydrogen Bonds in a Family of 9-Azaphenyl-9H-carbazoles

In order to demonstrate the possibility of intramolecular hydrogen bonds (IMHB) between an aromatic C-H and a pyridine nitrogen atom, the family of 9-arylcarbazoles , their 9-aryl-1-azacarbazole analogues and 9-phenyl-1,8-diazacarbazole (7), have been synthesized and the X-ray structure of all of them, expect 4, has been determined.The unit cell parameters are as follows.For 1: a=14.526(5) Angstroem, b=10.985(1) Angstroem, c=18.094(2) Angstroem, β=113.45(2) deg, V=2649(1) Angstroem3, Z=8, P21/n.For 2: a= 14.625(4) Angstroem, b=11.685(6) Angstroem, c=16.636(1) Angstroem, β=114.07(4) deg, V=2596(3) Angstroem3, Z=8, P21/n.For 3: a=25.76(2) Angstroem, b=5.200(6) Angstroem, c=19.47(1) Angstroem, β=112.07(5) deg, V=2417 Angstroem3, Z=8, C2/c.For 5: a=12.825(2) Angstroem, b=12.336(4) Angstroem, c=16.468(6) Angstroem, β=111.41(3) deg, V=2426(2) Angstroem3, Z=8, P21/n.For 6: a=10.682(3) Angstroem, b=29.033(9) Angstroem, c=7.524(3) Angstroem, β=90.46(3) deg, V=2333(1) Angstroem3, Z=8, P21/c.For 7: a=10.895(2) Angstroem, b=13.407(4) Angstroem, c=17.552(6) Angstroem, β=107.81(2) deg, V=2441(2) Angstroem3, Z=8, P21/c.The data were obtained at 293 K except for compound 7 for which the experimental temperature was 200 K.All compounds except 3 exist in the crystal in two different conformations.The potential curves corresponding to the rotation about the N(9)-C(aryl) bond of nine compounds (1-7 plus the nonsynthesized 2-pyridyl- and 2-pyrimidinyl-1,8-diaza analogues) have been calculated.The crystallographic torsion angles are near the zone of minimum energies according to AM1 calculations, save in the case of compound 1 (9-phenylcarbazole) where one of the independent molecules has a torsion angle of 78.4 deg, much larger than calculated.The calculated barrier through the planar state, ΔE0, contains much information and appears to be related to the 1H and 13C chemical shifts of some selected molecules.Compound 3 , with a torsion angle of 7.4(4) deg, is the clearest representative of the existence of C-H...N IMHBs.