Structurally-defined direct C-magnesiation and C-zincation of N-heterocyclic aromatic compounds using alkali-metal-mediated metallation

Demonstrating direct synergic low polarity metallation, 1-methylindole is C-magnesiated by (TMEDA)(2)center dot Na2MgBu4 and C-zincated by (TMEDA)center dot Na(Bu-t)(TMP)Zn(Bu-t), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised.