Facile synthesis of 2,5-diarylthiazoles via palladium-catalyzed tandem C-H substitutions. Design of tunable light emission and liquid crystalline characteristics.
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.
Mori
Atsunori
A
Chemical Resources Laboratory, Tokyo Institute of Technology, 4259 Nagatsuta, Yokohama 226-8503, Japan. amori@res.titech.ac.jp
Sekiguchi
Akitoshi
A
Masui
Kentaro
K
Shimada
Tomohiro
T
Horie
Masaki
M
Osakada
Kohtaro
K
Kawamoto
Masuki
M
Ikeda
Tomiki
T