Student Research: Justin Alvarez & Dr. Yalan Xing
Benzylic Amination By Ritter-Type Reaction via Mesolytic Cleavage
The goal of Dr. Xing and Justin’s research is to create stable benzylic carbocations capable of situ nucleophilic substitution reactions by combining the benefits of electrocatalysis and mesolytic cleavage. The two are especially interested in using Ritter-Reaction Analogs with nitriles to create amides due to their biological implications.
Justin shared that their research was inspired by the work of other synthetic organic chemists; he explained that they typically use electrocatalysts while completing their research. Electrocatalysts are so appealing because of their high sustainability, mild reaction conditions, and their high functional group compatibility. The electrocatalytic methods used while completing this research abide by the principles of green chemistry: less hazardous synthesis, design for energy efficiency, catalysis (versus stochiometric), and inherently benign chemistry for accident prevention. By use of a TEMPO group (2, 2, 6, 6-Tetramethylpiperidin-l-yl)oxyl) at the benzylic position, benzylic carbocation was formed upon single-electron oxidation of the tempolated-substrate. The nitrogen atom in the TEMPO benzylic group will assume a radical carbocation, sparking a spontaneous mesolytic cleavage at the now weakened C-O Bond.
