Generation and Reactivity of α-Amino-Substituted Arylmethyllithium Organometallics

Reductive cleavage of open chain and cyclic α-N,N-dialkylamino-substituted benzyl alkyl ethers 1a–f with a dispersion of Li metal and a catalytic amount of naphthalene in THF, allowed easy access to a wide array of α-N,N-dialkylamino-substituted benzyllithium derivatives. Reaction of these organometallics with various electrophiles afforded the expected products in satisfactory yields.