The superiority of properly prepared lithium 1-N,N-dimethylaminonaphthalenide (LDMAN) over other aromatic radical-anions for the generation of organolithiums by reductive lithiation

The use of lithium 1-N,N-dimethylaminonaphthalenide (LDMAN) is found to be considerably superior in yield, ease of operation, and cost to the far more widely used lithium p,p′-di-tert-butylbiphenylide (LDBB) in reductive lithiations by aromatic radical-anions to produce organolithium compounds, provided that careful temperature control is maintained during the generation of LDMAN. The main reason for the superiority is the great ease of separation of the aromatic byproduct dimethylaminonaphthalene by a dilute acid wash.