Quinazoline-Directed C-H Bond Functionalization Catalyzed by Ruthenium(II) Carboxylate - Construction of Polyconjugated Aryl-Heteroaryl Systems

A series of coupling products have been prepared by a ruthenium(II)-catalyzed direct ortho-C-H arylation of 2-(aryl/heteroaryl)-substituted quinazolines with (hetero) aryl bromides. Tri(hetero)aryl-substituted alkenes were also prepared by olefinic C-H activation of 2-(2-arylvinyl)quinazoline derivatives. High conversions and selectivities were achieved by choosing the appropriate ruthenium(II) carboxylate catalyst system, solvent, and reaction temperature. The possibility of a C(sp(3))-H functionalization by applying an arylation/reduction reaction sequence was also demonstrated.