Sodium Dialkyl-amidozincates: Alkyl or Amido Bases? An Experimental and Theoretical Case Study.

This article reports that alkali metal zincates are fast establishing themselves as a new vanguard class of organozinc reagent, to add to the old guard of organozinc halides and diorganozincs. Among the best developed alkali metal zincates are homoleptic triorganozincates and heteroleptic diorgano-amidozincates. In the latter category, lithium di-tert-butyltetramethylpiperidinozincate is receiving special attention in view of its high chemo-/regioselectivity in deprotonative reactions of, for example, functionalized aromatics and functionalized heteroaromatics.