Generation and Reactivity of a-Amino-Substituted Arylmethyllithium Organometallics

Reductive cleavage of open chain and cyclic alpha-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 alpha-N,N-dialkylamino-substituted benzyllithium derivatives. Reaction of these organometallics with various electrophiles afforded the expected products in satisfactory yields