Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C-H functionalization

Ryan Pearson, Shuyu Zhang, Gang He, Nicola Edwards, Gong Chen

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)891-899
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - May 8 2013

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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