Preparation of 2- and 5-Aryl Substituted Thiazoles via Palladium-Catalyzed Negishi Cross-Coupling
- 31 December 2001
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2001 (01) , 0128-0134
- https://doi.org/10.1055/s-2001-9753
Abstract
2-Aryl substituted thiazoles 3a-k were prepared by oxidative insertion of zinc into 2-bromothiazole (1) followed by palladium(0)-catalyzed Negishi cross-coupling in a one-pot procedure. 5-Aryl substituted thiazoles 6a-i were prepared by regioselective C-5 lithiation of 2-(trimethylsilyl)thiazole (4) follwed by transmetalation with zinc chloride and palladium(0)-catalyzed Negishi cross-coupling in a one-pot procedure. The synthetic sequences were combined to give 2,5-diaryl substituted thiazoles 8a, b and 10 via stepwise C-2 and C-5 arylation and vice versa.Keywords
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