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

Serena Mantenuto; Cecilia Ciccolini; Simone Lucarini; Giovanni Piersanti; Gianfranco Favi; Fabio Mantellini

doi:10.1021/acs.orglett.6b03775

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

Org Lett. 2017 Feb 3;19(3):608-611. doi: 10.1021/acs.orglett.6b03775. Epub 2017 Jan 17.

Authors

Serena Mantenuto¹, Cecilia Ciccolini¹, Simone Lucarini², Giovanni Piersanti², Gianfranco Favi¹, Fabio Mantellini¹

Affiliations

¹ Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino "Carlo Bo" , Via I Maggetti 24, 61029 Urbino, Italy.
² Department of Biomolecular Sciences, Section of Chemistry, University of Urbino "Carlo Bo" , Piazza Rinascimento 6, 61029 Urbino, Italy.

PMID: 28094964
DOI: 10.1021/acs.orglett.6b03775

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.

Publication types

Research Support, Non-U.S. Gov't