Tetradentate ligand, Tris(2-pyridylmethyl)amine (TPMA) has resulted in the formation of highly active and stable copper complexes used for catalyzing various radical processes such as atom transfer radical addition (ATRA), cyclization (ATRC) and polymerization (ATRP). ATRA and ATRC are the fundamental organic transformations used to generate C-C bond via addition of the alkyl halides across alkene in the presence of the reducing agents. In pursuit to design even more active catalytic system to activate C-X (X= Cl, Br) bond of less active alkyl halides, we tailored three new ligands 1-(5-methoxy-4,6-dimethylpyridin-2-yl)-N,N-bis(pyridin-2-ylmethyl)methanamine (TPMA*), bis(5-methoxy-4,6-dimethylpyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine(TPMA2*), tris((5-methoxy-4,6-dimethylpyridin-2-yl)methyl)amine (TPMA3*) with TPMA backbone in which the electron-donating groups such as methyl and methoxy are attached at 3,4,5 position on the pyridine rings. Using these ligands,xsic novel copper based catalytic systems were synthesized and characterized using IR, UV-Vis spectroscopy, cyclic voltammetry and single X-ray crystallography.      

Ligand design based on tetradentate tris(2-pyridylmethyl)amine (TPMA) skeleton for copper catalyzed atom transfer radical addition (ATRA)

248th National Meeting (2014)

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