Synthesis of N-Methyl-N-Phenylglycine Derivatives for the Electrochemical Synthesis of N-Aryl Iminium Ions

• Asher Chamuel, Chemistry, University of Delaware

• William Chain, Chemistry, University of Delaware

Tetrahydroquinolines are nitrogen heterocycles found in several natural products and pharmaceutically relevant compounds with biological properties. Current synthetic procedures to construct the tetrahydroquinoline core involve toxic and costly reagents that can be avoided using electrochemistry. The non-Kolbe electrolysis of N-phenyl amino acids provides access to reactive iminium ion intermediates. This two-electron oxidative electrolysis allows for a diverse array of new bond formations, including the [4+2] cycloaddition of tetrahydroquinolines. We have provided a three-step synthesis of N-phenylsarcosine substrates, to undergo the non-Kolbe electrolysis, with up to 88% yields.