Issue 10, 2024

Modular synthesis of C2-symmetric nitrogen-containing polyaromatics via visible light-enabled reductive aza-6π electrocyclization

Abstract

Nitrogen-containing polyaromatic compounds (N-PACs) show wide applications in synthetic chemistry and materials science, but their highly efficient preparation with structurally precise control is a big challenge. Herein, we report an unprecedented one-step modular construction of C2-symmetric N-PACs through visible-light-enabled tandem two-fold direct reduction/aza-6π electrocyclization of nitroarenes with benzaldehydes. This protocol provides a facile and versatile strategy for straightforward access to diverse N-PACs with good yields and excellent functional group compatibility under mild metal-free conditions. More importantly, the resultant C2-symmetric N-PAC 3ad could be readily converted into dicationic ammonium salt Me-3ad, which proved to be a powerful organic photocatalyst for C–H amination and trifluorometlylation.

Graphical abstract: Modular synthesis of C2-symmetric nitrogen-containing polyaromatics via visible light-enabled reductive aza-6π electrocyclization

Supplementary files

Article information

Article type
Research Article
Submitted
23 Jan 2024
Accepted
19 Mar 2024
First published
22 Mar 2024

Org. Chem. Front., 2024,11, 2884-2890

Modular synthesis of C2-symmetric nitrogen-containing polyaromatics via visible light-enabled reductive aza-6π electrocyclization

Q. Zhang, Q. Fan, Y. Zhou, J. Zhang and F. Zhang, Org. Chem. Front., 2024, 11, 2884 DOI: 10.1039/D4QO00140K

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