Bu₄NI Catalyzed C-H Activation Of Tertiary Amines To Construct α-cyano Amines And Tetrahydroquinolines

Unlike traditional transitional-metal catalysts still employed in a majority of C-Hfunctionalizations, Bu4NI, exhibits the similar reactivity while promoting the reactionsunder milder conditions at lower cost. In my master’s thesis, my focus is the Bu4NIcatalyzed constructions of-cyano amines and tetrahydroquinolines via the C-H activationof tertiary amines.The first part of my master’s thesis is the synthesize of-cyano amines:The-aminoalkyl radical generated from the C-H functionalization of tertiary aminescatalyzed by Bu4NI attacks the C-N triple bond of Benzoyl cyanide to form the-cyanoamines followed by the an elimination step of an acyl radical.The second part of my master’s thesis is the preparation of tetrahydroquinolines:Nucleophilic addition of the-aminoalkyl radical to the electron-deficient alkenesunder the Bu4NI catalysis followed by cyclization and aromatization steps provides thedesired tetrahydroquinolines.Compared with the previous methodologies, these two C-H functionalizations aredistinguished by free transition-metal catalysts, milder conditions and lower cost.