(281b) Continuous N-Hydroxyphthalimide Mediated Electrochemical Aerobic Oxidation of Benzylic C-H Bonds

Mo, Y., Massachusetts Institute of Technology
Jensen, K. F., Massachusetts Institute of Technology
Electroorganic chemistry has emerged as an environmentally benign tool for synthetic chemists to achieve efficient transformations that are challenging with traditional reagent-based methods. Continuous flow chemistry brings pharmaceutical industry numerous advantages, but implementing electroorganic synthesis in flow is challenging, especially for electroorganic reactions with coupled electrode reactions and slow chemical reactions. Here, we present an electrolysis flow cell engineered for the N-hydroxyphthalimide (NHPI) mediated electrochemical aerobic oxidation of benzylic C-H bonds. Measuring the kinetics of the chemical reaction with cyclic voltammetry gives insights into effects of molecular structure on reaction rate and explains the need for recycling to achieve good yields.