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Synthesis of Nitrogen-Containing Polyaromatics by Aza-Annulative π-Extension of Unfunctionalized Aromatics

Synthesis of Nitrogen-Containing Polyaromatics by Aza-Annulative π-Extension of Unfunctionalized Aromatics

Kou P Kawahara, Wataru Matsuoka, Hideto Ito, Kenichiro Itami

Angew Chem Int Ed Engl. 2020 Apr 16;59(16):6383-6388.

PMID: 32011794

Abstract:

Nitrogen-containing polycyclic aromatic compounds (N-PACs) are an important class of compounds in materials science. Reported here is a new aza-annulative π-extension (aza-APEX) reaction that allows rapid access to a range of N-PACs in 11-84 % yields from readily available unfunctionalized aromatics and imidoyl chlorides. In the presence of silver hexafluorophosphate, arenes and imidoyl chlorides couple in a regioselective fashion. The follow-up oxidative treatment with p-chloranil affords structurally diverse N-PACs, which are very difficult to synthesize. DFT calculations reveal that the aza-APEX reaction proceeds through the formal [4+2] cycloaddition of an arene and an in situ generated diarylnitrilium salt, with sequential aromatizations having relatively low activation energies. Transformation of N-PACs into nitrogen-doped nanographenes and their photophysical properties are also described.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP26042637	Silver hexafluorophosphate		26042-63-7	Price

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