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


European Journal of Organic Chemistry

Bogdan Štefane, Helena Brodnik Žugelj, Uroš Grošelj, Petra Kuzman, Jurij Svete, Franc Požgan

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(sp3)–H functionalization by applying an arylation/reduction reaction sequence was also demonstrated.

Read article: Eur. J. Org. Chem., 2017, 1855-1864