Preparation of 2- and 5-Aryl Substituted Thiazoles via Palladium-Catalyzed Negishi Cross-Coupling

Jacob Jensen; Niels Skjaerbaek; Per Vedsø

doi:10.1055/s-2001-9753

Synthesis 2001; 2001(1): 0128-0134
DOI: 10.1055/s-2001-9753

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Preparation of 2- and 5-Aryl Substituted Thiazoles via Palladium-Catalyzed Negishi Cross-Coupling

Jacob Jensen^* , Niels Skjaerbaek, Per Vedsø

^*Department of Organic Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark; Fax +45 43 30 30; E-mail: ns@acadia-pharm.com

Abstract

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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.

thiazoles - cross-coupling - arylation - zinc - lithiation

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