Palladium Complex Bearing 3,5-Bis(benzotriazol-1-Ylmethyl)toluene Ligand Catalyzes Oxidative Amination of Allyl Butyl Ether

Abstract

The reaction of 3,5-bis(bromomethyl)toluene with benzotriazole yields the bidentate ligand 3,5-bis(benzotriazol-1-ylmethyl)toluene (1). This ligand reacts with [PdCl 2 (cod)] (cod = 1,5-cyclooctadiene) to give the complex [PdCl 2 {3,5-bis(benzotriazol-1-ylmethyl)tolyl}] (2). These compounds were characterized by elemental analyses, mass spectra, and FTIR and NMR ( 1 H, 13 C) spectroscopies. The palladium(II) complex 2 shows high activity as catalyst for oxidative amination, involving allyl butyl ether and phthalimide as substrates and PhICl 2 as a stoichiometric oxidant.

Antibacterial Activities of Azole Complexes Combined with Silver Nanoparticles

“…All reagent-grade solvents were dried, distilled, and stored under a nitrogen atmosphere. The starting compounds were prepared based on the literature: bis(3,5-dimethyl-1-pyrazolyl)methane [ 38 ], bis(1,2,4-triazol-1-yl)methane [ 39 ], 3,5-bis(3,5-dimethylpyrazol-1-ylmethyl)toluene [ 40 ], 3,5-bis(benzotriazol-1-ylmethyl)toluene [ 41 ] and 1,3-bis(indazol-1-ylmethyl)benzene (L). The synthetic protocols for the previously reported complexes dichloro[bis(3,5-dimethylpirazol-NN)]cobalt(II) ( 1 ), dichloro[bis(3,5-dimethylpirazol-NN)]-copper(II) ( 2 ), dichloro[bis(3,5-dimethyl-1-pyrazolyl)methane-NN]cobalt(II) ( 3 ), dichloro[bis(3,5-dimethyl-1-pyrazolyl)methane-NN]copper(II) ( 4 ), dichloro[bis(1,2,4-triazol-1-yl)methane-NN]-cobalt(II) ( 9 ) and dichloro[bis(1,2,4-triazol-1-yl) methane-NN]copper(II) ( 10 ) are provided in the Supplementary Information [ 8 ].…”

Crystal structure of 1,3-bis(1H-benzotriazol-1-ylmethyl)benzene

“…In these complexes, the metal center coordinates through the N3-nitrogen of the benzotriazole ring (O'Keefe & Steel, 2000). We have been interested in the synthesis of metal complexes with ligands derived from benzotriazole, which show high activity as catalysts for oxidative amination of allyl butyl ether (Hurtado et al, 2013).The crystal structures for a number of bis(1H-benzotriazol-1-ylmethyl)arene ligands have been determined: 2,6bis(1H-benzotriazol-1-ylmethyl)pyridine (Selvanayagam et al, 2002), 1,4-bis(1H-benzotriazol-1-ylmethyl)benzene tetrahydrate (Cai et al, 2004) and benzyl 3,5-bis(1H-benzotriazol-1-ylmethyl)phenyl ether (Selvanayagam et al, 2004). As part of structural studies of the self-assembly process of metal ions with ligands derived from benzotriazole, we report here the crystal structure of the ligand 1,3-bis(1H-benzotriazol-1-ylmethyl)benzene.…”

Coordination Polymers Containing 1,3-Phenylenebis-((1H-1,2,4-triazol-1-yl)methanone) Ligand: Synthesis and ε-Caprolactone Polymerization Behavior

“…Although mononuclear, binuclear and coordination polymers have been obtained using related bis(azolyl) ligands [ 26 , 27 , 28 , 29 , 30 ], in our case, the isolation of non-soluble compounds indicates the probable formation of a polymeric species for 2 , 3 and 5 . This assumption is supported by the results from both experimental and computational studies, and it was possible to propose structures of metal complexes (coordination polymers) as shown in Figure 4 .…”