Facile Synthesis of 2,5-Diarylthiazoles via Palladium-Catalyzed Tandem C−H Substitutions. Design of Tunable Light Emission and Liquid Crystalline Characteristics

Abstract

A mild and regioselective C-H substitution reaction of thiazole by the catalysis of the palladium/copper system is found to proceed in the presence of tetrabutylammonium fluoride under mild conditions. Applying the new reaction, we synthesized various 2,5-diarylthiazoles that exhibit light-emitting and liquid crystalline characteristics in good yields. The color of light emission is tunable by the introduction of the substituent. Differently substituted 2,5-diarylthiazoles are found to exhibit a stable liquid crystal phase in a wide temperature range.