We report the metalation of the 1,3,4-oxadiazole
and 1,2,4-triazole scaffolds via regioselective zincation or magnesiation
using the TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) TMP2Zn·2LiCl, TMP2Zn·2MgCl2·2LiCl,
TMPMgCl·LiCl, and TMPZnCl·LiCl under mild conditions in
THF. Subsequent trapping with various electrophiles including hydroxylamino
benzoates gives access to functionalized heterocycles while tolerating
many functional groups.