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

Abstract

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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Publication details

The article was received on 26 Jun 2018, accepted on 02 Aug 2018 and first published on 09 Aug 2018


Article type: Edge Article
DOI: 10.1039/C8SC02802H
Citation: Chem. Sci., 2018, Accepted Manuscript
  • Open access: Creative Commons BY license
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    Annulative π-Extension of Indoles and Pyrroles with Diiodobiaryls by Pd Catalysis: Rapid Synthesis of Nitrogen-Containing Polycyclic Aromatic Compounds

    H. Kitano, W. Matsuoka, H. Ito and K. Itami, Chem. Sci., 2018, Accepted Manuscript , DOI: 10.1039/C8SC02802H

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