Issue 3, 2025

Practical heptafluoroisopropylation of nitrogen-containing (hetero)aromatics under visible light

Abstract

A practical visible-light-driven heptafluoroisopropylation of substituted anilines and heterocyclic aromatics has been achieved. The key to the success of this facile transformation lies in the in situ generation of a novel electron donor–acceptor (EDA) complex between trimethyl phosphite and heptafluoroisopropyl iodide, which enables the formation of diverse heptafluoroisopropylated products in a regio-selective fashion under mild reaction conditions. In addition, the present EDA protocol demonstrates applicability for other perfluoroalkylation reactions. This work features high site-selectivity, transition-metal and photosensitizer free conditions, and broad substrate scope, constituting a greener alternative to access synthetically important perfluoroalkyl-containing molecules, such as Broflanilide.

Graphical abstract: Practical heptafluoroisopropylation of nitrogen-containing (hetero)aromatics under visible light

Supplementary files

Article information

Article type
Research Article
Submitted
06 Sep 2024
Accepted
23 Nov 2024
First published
26 Nov 2024

Org. Chem. Front., 2025,12, 800-807

Practical heptafluoroisopropylation of nitrogen-containing (hetero)aromatics under visible light

X. Luo, S. Lou, Y. Sun, C. Jing, X. Fei, X. Zhang, J. Zhai, Y. Wang and D. Xu, Org. Chem. Front., 2025, 12, 800 DOI: 10.1039/D4QO01660B

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