Tetrahedron

Synthesis of 2-TIPS-oxazol-5-ylboronic acid pinacol ester: efficient route to 5-(het) aryloxazoles via Suzuki cross-coupling reaction

N Primas, A Bouillon, JC Lancelot, S Rault

Index: Primas, Nicolas; Bouillon, Alexandre; Lancelot, Jean-Charles; Rault, Sylvain Tetrahedron, 2009 , vol. 65, # 32 p. 6348 - 6353

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Citation Number: 8

Abstract

5-Aryloxazoles have traditionally been synthesized by the van Leusen reaction which consists of a condensation between carbonyl compounds and tosylmethylisocyanide (TosMIC). 3, 3a, 3b, 3c and 4f Metal-catalyzed direct heterocycle C–H arylation was a relative new method to introduce aryl groups in the 2 or 5 position. 4, 4a, 4b, 4c, 4d and 4e However, this straightforward approach is penalized by the regioselectivity difficulties in particular with unsubstituted ...