Bidentate Ligand Driven Intramolecularly Te…O Bonded Organotellurium Cations from Synthesis, Stability to Catalysis

A new series of unsymmetrical phenyl tellurides derived from 2-N-(quinolin-8-yl) benzamide ligand has been synthesized in a practical manner by the copper-catalyzed method by using diaryl ditelluride and Mg as a reductant at room temperature. In order to augment the Lewis acidity of these newly formed unsymmetrical monotellurides, these have been transformed into corresponding unsymmetrical 2-N-(quinolin-8-yl)benzamide tellurium cations. Subsequently, these Lewis acidic tellurium cations were used as chalcogen bonding catalysts, enabling the synthesis of various substituted 1,2-dihydroquinolines by activating ketones with anilines under mild conditions. Moreover, the synthesized 2-N-(quinolin-8-yl)benzamide phenyl tellurium cation has also catalyzed the formation of β-amino alcohols in high regioselectivity by effectively activating epoxides at room temperature. Mechanistic insight by ¹ H and ¹⁹ F NMR study, electrostatic surface potential (ESP map), control reaction in which tellurium cation reacted explosively with epoxide, suggested that the enhanced Lewis acidity of tellurium center seems responsible for efficient catalytic activities under mild conditions enabling β-amino alcohols with excellent regioselectivity and 1,2-dihydroquinolines with trifluoromethyl_, nitro, and pyridylsubstitution, which were difficult to access.