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Relevant academic research and scientific papers

Diaryltriazenido Palladium(II) complexes derived from 1-(2-bromo-4-ethoxycarbonylphenyl)-3-phenyltriazenes

1-(2-Bromo-4-ethoxycarbonylphenyl)-3-phenyltriazene (1) can easily be deprotonated yielding the corresponding triazenides of lithium, silver, or triethylammonium. The equimolar metathesis reaction of [(Ph3P)2PdCl2] with th

2-Halo- and/or 4-ethoxycarbonyl-substituted asymmetric 1,3-diaryltriazenes and 1,3-diarylamidines as well as N-methylated congeners

1,3-Diaryltriazenes Ar–N[dbnd]N–N(R)-R’ [R = H; Ar/R’ = C6H4-4-COOEt/Ph (1), C6H3-2-Br-4-COOEt/Ph (2), CH2Ph/C6H4-4-COOEt (3)] and the N-methylated congeners [R = Me; Ar/R’ = Cs

Mechanistic investigations on C-H activated dealkylating cyclo-amination reactions of substituted triazenes, formamidines and amidines

Catalytic dealkylating cycloamination reactions of N 1-methylated-N 1,N 3-diarylated triazenes proceed via two subsequent oxidative addition reactions, regioselectivity producing benzotriazoles by C-H and C-Br activation steps. Whereas palladium-based catalysis in the presence of dealkylating reagents and directing phosphane ligands leads to high yields, the homologous metals nickel and platinum as well as other 3d transition metals show only poor catalytic activity in similar procedures. Starting compounds have been widely varied to introduce potentially competing reaction sites and to investigate the reaction mechanism of the catalytic cyclization reactions. Yields of the benzotriazole synthesis strongly depend on the electronic and steric properties of the directing phosphane ligands, the nature of the dealkylating bases and the substitution pattern in 2- A nd 4-position of the aryl groups of the starting triazenes. In order to clarify the role of the catalyst, palladium-based intermediates were identified. Finally, formamidines and bulky amidines were tested in related C-H activated dealkylating cycloamination reactions.

Palladium-nanoparticle-catalyzed 1,7-palladium migration involving C-H activation, followed by intramolecular amination: Regioselective synthesis of N 1-arylbenzotriazoles and an evaluation of their inhibitory activity toward indoleamine 2,3-dioxygenase

A sulfur-modified gold-supported palladium material (SAPd) has been developed bearing palladium nanoparticles on its surface. Herein, we report for the first time the use of SAPd to affect a Pd-nanoparticle-catalyzed 1,7-Pd migration reaction for the synthesis of benzotriazoles via C-H bond activation. The resulting benzotriazoles were evaluated in terms of their inhibitory activity toward indoleamine 2,3-dioxygenase.

1,7-palladium migration via C-H activation, followed by intramolecular amination: Regioselective synthesis of benzotriazoles

A novel 1,7-palladiummigration-cyclization-dealkylation sequence for the regioselective synthesis of benzotriazoles has been developed. These reactions proceed in excellent yields with high regioselectivities. The mechanism of the reaction has also been investigated.