ChemInform Abstract: Synthesis of 1,3‐Diarylated Imidazo[1,5‐a]pyridines with a Combinatorial Approach: Metal‐Catalyzed Cross‐Coupling Reactions of 1‐Halo‐3‐arylimidazo[1,5‐a]pyridines with Arylmetal Reagents.

Abstract

Fused pyridine derivatives R 0450 Synthesis of 1,3-Diarylated Imidazo[1,5-a]pyridines with a Combinatorial Approach: Metal-Catalyzed Cross-Coupling Reactions of 1-Halo-3-arylimidazo[1,5-a]pyridines with Arylmetal Reagents. -Selective halogenation of a variety of substrates (I) is achieved. Only (Ig), bearing a highly electron-rich 4-methylaminophenyl group fails to provide the iodo derivative. Iodinated and brominated products are further applied to Kumada-Tamao-Corriu [→ cf. (IV)] and Suzuki-Miyaura [cf. (VII)] cross-coupling protocols. Photophysical properties, UV/vis and fluorescent spectra of the diarylated products are studied. -(SHIBAHARA*, F.; YAMAGUCHI, E.; KITAGAWA, A.; IMAI, A.; MURAI*, T.; Tetrahedron 65 (2009) 26, 5062-5073; Dep. Chem., Fac. Eng., Gifu Univ., Yanagido, Gifu 501-11, Japan; Eng.) -Y. Steudel 44-154