Combining two relatively weak bases (Zn(TMP)₂ and KOtBu) for the regioselective metalation of non-activated arenes and heteroarenes.

ABSTRACT: Co-operation between two relatively weak Brønsted bases, Zn(TMP)₂ and KOtBu, produces a bimetallic base strong enough to regioselectively zincate non-activated arenes such as naphthalene, biphenylene and anthracene under mild conditions. This co-operativity is also effective with a range of more sensitive five-membered ring heterocyclic substrates including benzoxazole and caffeine. Metalation products have been intercepted with iodine, affording the relevant iodo-(hetero)arenes in good to excellent yields with finely tuned regioselective control. Combining NMR spectroscopic and X-ray crystallographic studies has uncovered that depending on the solvent, a complicated ligand distribution process of mixed aryl/alkoxy higher order zincate intermediates, (THF) _n</

SUBMITTER: Judge NR 

PROVIDER: S-EPMC11334761 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature