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Additive-Free EDA Photochemical Arylative Trifluoromethylation of Enamides with Trifluoromethyl Benzothiazole Sulfones

Rui Lv, Lujun Lou, Tianshuai Zhu, Jing‐Jing Zhang, Guangwei Wu, Mengyang Hu, Lijun Tang, Zhen Chen

2025Organic Letters8 citationsDOI

Abstract

An additive-free trifluoromethylation–heteroarylation of enamides with trifluoromethyl heteroaryl sulfones via EDA photochemistry is reported. Under visible-light irradiation, diverse enamides and sulfones undergo efficient difunctionalization to afford CF 3 -heteroaryl amides in moderate to excellent yields, without the need for photocatalysts or additives. Mechanistic studies support the formation of a photoexcited EDA complex that triggers C–S bond cleavage, generating CF 3 and heteroaryl anions. This work provides a sustainable approach to alkene arylative difunctionalization and expands the utility of aryl sulfones in constructing CF 3 -containing scaffolds.

Topics & Concepts

TrifluoromethylationChemistryTrifluoromethylAlkeneCombinatorial chemistryArylFluorineBond cleavageBenzothiazolePhotochemistryOrganic chemistryAlkylCatalysisFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions
Additive-Free EDA Photochemical Arylative Trifluoromethylation of Enamides with Trifluoromethyl Benzothiazole Sulfones | Litcius