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.
Palladium(II)-Catalyzed Intramolecular Oxidative C−H/C−H Cross-Coupling Reaction of C3,N-linked Biheterocycles: Rapid Access to Polycyclic Nitrogen Heterocycles
MANTENUTO, SERENA;CICCOLINI, CECILIA;LUCARINI, SIMONE;PIERSANTI, GIOVANNI;FAVI, GIANFRANCO;MANTELLINI, FABIO
2017
Abstract
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.File in questo prodotto:
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