Coupling of Arylamines with Coordinated Arylazopyrimidines in Palladium(II) Complexes

Abstract

Keywords: Nitrogen heterocycles / Palladium / N ligands / Aminations / X-ray structure / EHMO calculation 2-(Arylazo)pyrimidine (1) reacts with palladium chloride and gives Pd(aapm)Cl 2 (2) which undergoes a palladium(II)-mediated novel carbon−nitrogen bond formation reaction of the aromatic amines to the ortho-C−H function of the pendant aryl ring in the coordinated 2-(arylazo)pyrimidine. The reactant, Pd(papm)Cl 2 (2a) and the product, Pd(papm-N-C 6 H 4 -OCH 3 -p)Cl (5a) have been characterised by X-ray crystal structure. The coupled products exhibit low energy trans-

Palladium(II)-iodo-{1-alkyl-2-(arylazo)imidazole} complexes: Synthesis, structure, dynamics of photochromism and DFT computation

“…On appending Ar-N@N-to the backbone of N-heterocycle p-deficient azoheterocycles like arylazopyridine, arylazopyrimidine, arylazoimidazole, etc. have been synthesized [3][4][5][6][7]. Arylazopyridine undergoes light stimulated reversible trans-cis isomerization about -N@N-bond.…”

“…Towards the exploration of photo switching activity and metal ion binding the design of azoheterocycles become an exciting area for the last few years of research [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. We have used 1-alkyl-2-(arylazo)imidazole (Raai-C n H 2n+1 ) to characterize coordination chemistry of transition and non-transition metal ions [18][19][20][21][22]. Azoimidazole derivatives like, 1-N-(ribofuranosyl)-2-phenylazoimidazole has shown trans-cis photoisomerization upon irradiation with UV light [23].…”

“…4 ] in the mixture of methanol and ethylene glycol monomethyl ether (EGME). An orange crystalline compound is separated at room temperature.…”

Synthesis and characterization of stable thiazolylazo anion radical complexes of ruthenium(II)

“…Aryl-azo-heterocyclic ligands bearing the azoimine function -N=N-C=N-have excellent ability to stabilize low valent metal redox states and are useful in metal-assisted organic transformation reactions and as metallochromic indicators and also show photochromic behavior [14][15][16][17][18][19][20][21][22][23][24][25][26]. An interesting property of these ligands is their ability to generate anion radical complexes by the addition of one electron to the azo p* orbital (Scheme 1).…”

Interaction Between Pd(RaaiR/)Cl2 and HQ: Reaction Dynamics and Mechanism (RaaiR/ = 1-alkyl-2-(arylazo)imidazole; HQ = 8-Quinolinol)

“…Major aspects of research activities using -N=N-C=N-are the synthesis, spectroscopic characterization, structural studies, solution redox properties of transitional [1][2][3][4][5] and non-transitional metals [6,7]; analytical applications and metal ion separation from mixtures, ores, geological, and medicinal samples [8]; metal assisted unusual chemical transformation in the organic part leading to synthesis of new organic molecules [9][10][11]. RaaiR / belongs to azoimine family, -N=N-C=N-.…”