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Annulative π-Extension of Indoles and Pyrroles with Diiodobiaryls by Pd Catalysis: Rapid Synthesis of Nitrogen-Containing Polycyclic Aromatic Compounds

Hiroyuki Kitano, Wataru Matsuoka, Hideto Ito,* Kenichiro Itami*
Chem. Sci.
2018, Advance article. DOI: 10.1039/c8sc02802h

A palladium-catalyzed one-step annulative π-extension (APEX) reaction of indoles and pyrroles that allows rapid access to nitrogen-containing polycyclic aromatic compounds is described. In the presence of palladium pivalate and silver carbonate, diverse indoles or pyrroles coupled with diiodobiaryls in a double direct C–H arylation manner to be transformed into the corresponding π-extended compounds in a single step. The newly developed catalytic system enables the use of various pyrroles and indoles as templates with a series of diiodobiaryls to provide structurally complicated and largely π-extended nitrogen-containing polycyclic aromatic compounds that are otherwise difficult to synthesize.

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