Issue 1, 2025

Visible light-driven and substrate-promoted alkenyltrifluoromethylation of alkenes to synthesize CF3-functionalized 1,4-naphthoquinones

Abstract

The first example of the visible light-driven and substrate-promoted three-component alkenyltrifluoromethylation of alkenes is developed. This approach uses easily available alkenes, 2-arylamino-1,4-naphthoquinones and Togni reagent as the reactants, and describes good functionality tolerance. The reaction offers a precise synthesis of valuable CF3-functionalized 1,4-naphthoquinones and can be applied in late-stage modification of natural products and pharmaceuticals. Experimental results imply that bifunctional 2-arylamino-1,4-naphthoquinones serve as both substrates and catalysts. In terms of this autocatalytic system, the protocol enables a straightforward intermolecular difunctionalization of alkenes under visible light irradiation without external catalysts.

Graphical abstract: Visible light-driven and substrate-promoted alkenyltrifluoromethylation of alkenes to synthesize CF3-functionalized 1,4-naphthoquinones

Supplementary files

Article information

Article type
Paper
Submitted
29 Sep 2024
Accepted
31 Oct 2024
First published
01 Nov 2024

Org. Biomol. Chem., 2025,23, 151-156

Visible light-driven and substrate-promoted alkenyltrifluoromethylation of alkenes to synthesize CF3-functionalized 1,4-naphthoquinones

L. Tang, F. Jia, R. Yu, L. Zhang and Q. Zhou, Org. Biomol. Chem., 2025, 23, 151 DOI: 10.1039/D4OB01585A

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