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

Org Biomol Chem. 2024 Nov 8. doi: 10.1039/d4ob01585a. Online ahead of print.

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.