ArticleBeilstein journal of organic chemistry2013
Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C-H functionalization.
Article in Beilstein journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Palladium-Catalyzed Arylation of C(spACS omega · 2021Article
- Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.Beilstein journal of organic chemistry · 2014Review
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5 authors.
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Abstract
We report a new synthesis of phenanthridines based on palladium-catalyzed picolinamide-directed sequential C-H functionalization reactions starting from readily available benzylamine and aryl iodide precursors. Under the catalysis of Pd(OAc)2, the ortho-C-H bond of benzylpicolinamides is first arylated with an aryl iodide. The resulting biaryl compound is then subjected to palladium-catalyzed picolinamide-directed intramolecular dehydrogenative C-H amination with PhI(OAc)2 oxidant to form the corresponding cyclized dihydrophenanthridines. The benzylic position of these dihydrophenanthridines could be further oxidized with Cu(OAc)2, removing the picolinamide group and providing phenathridine products. The cyclization and oxidation could be carried out in a single step and afford phenathridines in moderate to good yields.
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