N-phenylpyrrole: A kinetic, though not thermodynamic preference for dilithiation

Article abstract of DOI:10.1016/S0040-4020(01)80556-1

Under appropriate conditions the clean preparation of either the α-monolithiated or the o,α-dilithiated derivative of N-phenylpyrrole is possible. In the latter case, the first deprotonation occurs at the α-position. Dimetalation is kinetically but not thermodynamically favored.