Amines coupling reactions

We synthesized uniform CU2O coated Cu nanoparticles from the thermal decomposition of copper acetylacetonate, followed by air oxidation. We successfully used these nanoparticles for the catalysts for Ullmann type amination coupling reactions of aryl chlorides. We synthesized core/shell-like Ni/Pd bimetallic nanoparticles from the consecutive thermal decomposition of metal-surfactant complexes. The nanoparticle catalyst was atom-economically applied for various Sonogashira coupling reactions. 

Synthesis of CU2O coated Cu nanoparticles and their successful applications to Ullmann-type amination coupling reactions of aryl chlorides... 

Scheme 3. Ullmann-type amination coupling reaction...

Dobson et al. (48JCS123) constructed this ring system by using the Ullmann-amine coupling reaction between 7-aminoquinoline 1 and potassium 2,4-dichlorobenzoate, followed by cyclization of the resultant diaryl-... 

Cyclocondensation of 2-aminobenzoylformic acid 98 and cyclohexane-1,2-dione dioxime 99, followed by decarboxylation with concomitant dehydrogenation of the diacid 100, gave quino[3,2-c]acridine 101 (Scheme 19) (70JPR1105). The same skeleton 102 was obtained from the Ullmann-amine coupling reaction of 2-aminobenzophenone and 1,2-diiodobenzene, followed by ring closure (85LA1501). 

Tml2, Dyh and Ndh have also been used in an acetonitrile/amine coupling reaction, which produced amidines of general formula MeC (=NH)NR R R R2 = H, Me H, iPr H, fBu Et2). The reaction is sub-stoichiometric in rare-earth diiodide but not really catalytic since part of the produced amidine remained tightly held aroimd the rare-earth metal it could be liberated by heating a trivalent intermediate formulated as Rl2(amidine)4(amidinate) (R = Nd, Dy, Tm) imder vacuum, and the residue could be recycled to produce more amidine. This reaction is not specific of the divalent iodides since many rare-earth triiodides were also effective. In the case of dysprosium and diethylamine, an intermediate trivalent amidine complex has been isolated and structurally characterised in the form of the zwitterionic [Dy MeC(=NH)NEt2 4][(I)3] (Bochkarev et al., 2007) (Figure 9). 

Son, S. U., Park, I. K., Park, J., and Hyeon, T. 2004. Synthesis of CujO coated Cu nanoparticles and their successful applications to Ulhnann-type amination coupling reactions of aryl chlorides. Chem. Commun. (7) 778-779. 

P. Li, L. Wang, Y. Zhang, M. Wang, Tetrahedron Lett. 2008, 49, 6650-6654. Highly efficient three-component (alde-hyde-alkyne-amine) coupling reactions catalyzed by a reusable PS-supported NHC-Ag(l) under solvent-free reaction conditions. 

Table 2 Photocatalytic aerobic amine coupling reaction based on 10 1 mol%10,CH3CN...

The A (aldehyde-alkyne-amine) coupling reaction represents a benchmark transformation to evaluate the catalytic activity of new NHC-Ag complexes. A variety of propargyl amines were efficiently synthesized by this method in the presence of diverse NHC-Ag complexes. In some cases, supported catalysts allowing recycling could also be used without loss of efficiency. ... 

Several p-block compounds have been employed in this acid-amine coupling reaction these include bismuth, indium and antimony. Indium metal has been found useful for the N-formylation of amines. This reaction requires only 10 mol% indium catalyst and can be used for formic acid reactions with amino alcohols resulting in no side reaction on the alcohol terminus. Electron-rich triarylbismuthanes have been reported to couple carbo>ylic acids to amines within reaction times of 12 hours. In numerous cases, high yields were obtained although little amine scope is explored and in some cases where hindered carbojq lic acids were used, only starting materials were recovered. ... 

Hyeon [21] synthesized uniform Cu20-coated Cu nanopaiticles from the thermal decomposition of copper acetylacetmie followed by air oxidation and used these nanoparticles as catalysts for UUmaim-type amination coupling reaction of aryl chlorides. 

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