Palladium(II)-Catalyzed Intramolecular Oxidative C–H/C–H Cross-Coupling Reaction of C3,N-Linked Biheterocycles: Rapid Access to Polycyclic Nitrogen Heterocycles

• DOI: 10.1021/acs.orglett.6b03775
• Publication Date: 2017-01-17T22:43:43Z
• Authors: Serena Mantenuto; Cecilia Ciccolini; Simone Lucarini; Giovanni Piersanti; Gianfranco Favi; Fabio Mantellini
• Keywords: 2. Zero hunger; 01 natural sciences; 3. Good health; 0104 chemical sciences

A Pd(II)-catalyzed intramolecular oxidative C-H/C-H cross-coupling has been developed for the direct construction of valuable polycyclic heteroarene scaffolds. From a retrosynthetic point of view, the strategic formation of a C-C bond via C(sp2)-H/C(sp2)-H dehydrogenative coupling across C3,N-linked biheterocyclic precursors may be useful in de novo syntheses of indole-derived natural products and pharmaceuticals. The reaction exhibited good functional group/heterocycle tolerance, and a proposed mechanism involving an azoylpalladium complex is also supported.