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Halogen-Bonding-Induced Hydrogen Transfer to C=N Bond with Hantzsch Ester

Wei He, Yi-Cen Ge and Choon-Hong Tan

Organic Letters, 2014, 16, 3244 – 3247


Abstract: Several bidentate dihydroimidazolines were prepared and investigated as catalysts for hydrogen transfer reduction of C=N bond with Hantzsch ester. Highly efficient reactions were observed for quinolines and imines with low catalyst loading of 2 mol %. The presence of halogen bonding was elucidated using NMR studies and isothermal calorimeric titrations. Binding constants of the XB donors were also measured using isothermal calorimeric titrations (ITC).


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