Search

The Chan–Lam reaction conditions were optimized for the synthesis of N-aryl derivatives of adamantane-containing amines. A number of adamantane-containing amines and diamines with different steric hindrances at the primary amino groups were reacted with p-tolylboronic acid under the optimized conditions [0.1 M solution of amine in MeCN, p-tolylboronic acid (2 equiv), DBU (2 equiv), copper(II) acetate (20 mol %), 25°C, 24 h]. The reactivity of the amines was found to strongly depend on their structure, and the maximum yield of the target products reached 74% from the monoamines and 66% from the diamines. [ABSTRACT FROM AUTHOR]

N-(Het)arylation of adamantane-containing amines with halonaphthalenes and haloquinolines catalyzed by either CuI or copper nanoparticles with an average size of 25 nm in the presence of 2-isobutyrylcyclohexanone, rac-BINOL, and l-proline as a ligand and Cs2CO3 as a base in DMSO at 110 °C was studied. The reactions proceed smoothly with 2-iodonaphthalene and 6-iodoquinoline, the possibility of successful reactions with 6- and 3-bromoquinolines was also shown. In the case of 1-bromonaphthalene, 5- and 8-bromoquinolines, only Pd-catalyzed amination can provide the high yields of the products. An alternative possibility of C(sp2)—N bond formation was studied employing the Chan—Lam reaction with of 2-naphthaleneboronic acid and pinacolates of 6- and 3-quinolineboronic acids. [ABSTRACT FROM AUTHOR]

The N-heteroarylation of n-octylamine and adamantane-containing amines with 2-iodopyridine and 2-bromopyridine and its fluorinated derivatives under the catalysis of CuI and copper nanoparticles in DMSO in the presence of various ligands was studied. 2-Isobutyrylcyclohexanone was found to be the most efficient ligand in the reactions catalyzed by CuI. In the reactions catalyzed by copper nanoparticles, 2-isobutyrylcyclohexanone or l-proline turned to be most active. The yields of the reactions catalyzed by copper nanoparticles were better than or equal to those in the CuI-catalyzed processes. The possibility of nanocatalyst recycling was studied, and its reuse in 6 cycles without loss of activity was demonstrated. [ABSTRACT FROM AUTHOR]

N-Arylation of n-octylamine and adamantane-containing amines with iodobenzene and its deriva-tives has been performed in DMSO using copper(I) iodide and copper nanoparticles in the presence of various ligands as catalysts. In all cases, 2-isobutyrylcyclohexanone turned out to be the most efficient ligand, and higher yields of the arylation products were obtained in the presence of copper nanoparticles. The nanocatalyst can be recycled 9 times without significant loss of yield. [ABSTRACT FROM AUTHOR]