Benzyllithium from methylated benzylamine and its ammonium salt via naphthalene-catalyzed carbon-nitrogen bond reductive cleavage

Abstract

The reaction of N,N-dimethylbenzylamine with lithium powder and a catalytic amount of naphthalene, followed by addition of different electrophiles, gave the expected reaction products in low yield. However, yields could be improved by using the corresponding ammonium salt instead of the amine. When N,N,N-trimethylbenzylammonium iodide was submitted to the naphthalene-catalyzed lithiation process, followed by reaction with several electrophiles, the expected reaction products were obtained in moderate to good yields.