Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 4, Pages 544-550Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo01290c
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Funding
- National Natural Science Foundation of China [21772236, 21472198]
- Fundamental Research Funds for the Central Universities
- South-Central University for Nationalities [CZQ17009, CZT18012]
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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 the 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 beta-hydride elimination, which may be controlled by the p-p stacking effect between the aryl group of the substrate and DMAP, demonstrated by primary mechanistic studies and X-ray data of the substrate-PdDMAP complex.
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