2-METALATED OXAZOLES - PKA DEPENDENT DEUTERATIONS, NMR-STUDIES AND PALLADIUM-CATALYZED COUPLINGS

Authors
CROWE E HOSSNER F HUGHES MJ
Citation
E. Crowe et al., 2-METALATED OXAZOLES - PKA DEPENDENT DEUTERATIONS, NMR-STUDIES AND PALLADIUM-CATALYZED COUPLINGS, Tetrahedron, 51(32), 1995, pp. 8889-8900
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
32
Year of publication
1995
Pages
8889 - 8900
Database
ISI
SICI code
0040-4020(1995)51:32<8889:2O-PDD>2.0.ZU;2-W
Abstract
Deuteration experiments on 2-lithiated oxazoles show a pKa dependent r egioselectivity suggesting that the ring cleaved tautomer dominates th e equilibrium. Transmetallation to the zinc derivative gives a species which behaves as a C2 ring closed nucleophile as judged by deuteratio n and palladium catalysed coupling experiments. These conclusions are supported by nmr spectroscopy studies of the metallated species.