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Practical Synthesis of Polysubstituted Unsymmetric 1,10-Phenanthrolines by Palladium Catalyzed Intramolecular Oxidative Cross Coupling of C(sp2)-H and C(sp3)-H Bonds of Carboxamides

Abstract

1,10-Phenanthroline derivatives are among the most commonly used ligands for organic synthesis. A short sequence for the practical synthesis of polysubstituted unsymmetric 1,10-phenanthroline compounds was developed based on palladium-catalyzed oxidative cross coupling reaction of C(sp2)-H/C(sp3)-H bonds of carboxamides. DMAP as a preferred ligand was crucial for the reaction to avoid the β-hydride elimination, which may be controlled by the π-π stacking effect between the aryl group of substrate and DMAP, demonstrated by primary mechanistic studies and X-ray data of substrate-Pd-DMAP complex.

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Publication details

The article was received on 29 Nov 2018, accepted on 08 Jan 2019 and first published on 09 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01290C
Citation: Org. Chem. Front., 2019, Accepted Manuscript
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    Practical Synthesis of Polysubstituted Unsymmetric 1,10-Phenanthrolines by Palladium Catalyzed Intramolecular Oxidative Cross Coupling of C(sp2)-H and C(sp3)-H Bonds of Carboxamides

    W. Sun, J. Liu and B. Wu, Org. Chem. Front., 2019, Accepted Manuscript , DOI: 10.1039/C8QO01290C

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