2-Metallated Oxazoles; pKa Dependent Deuterations, NMR Studies and Palladium Catalysed Couplings

Article abstract of DOI:10.1016/0040-4020(95)00498-W

Deuteration experiments on 2-lithiated oxazoles show a pKa dependent regioselectivity suggesting that the ring cleaved tautomer dominates the equilibrium.Transmetallation to the zinc derivative gives a species which behaves as a C2 ring closed nucleophile as judged by deuteration and palladium catalysed coupling experiments.These conclusions are supported by nmr spectroscopy studies of the metallated species.