Photocatalyst-Free Visible-Light-Induced Trifluoroalkylation of Electron-Deficient Heteroaromatics via a Three-Component Minisci-Type Reaction.
- 1Department of Organic Chemistry, University of Valencia, Avda. Vicent Andrés Estellés 22, Valencia, Spain, 46100-Burjasot
Abstract
The combination of electron-poor heterocycles and trifluoromethyl motifs is widely found in pharmaceuticals, making the development of methods for the simultaneous introduction of these two features highly desirable. Herein, we report a fast, acid-free, metal-free, photocatalyst-free, and operationally simple multicomponent approach for the trifluoroalkylation of electron-poor heterocycles under open-air conditions. The method relies on the ability of trifluoromethyl thianthrenium triflate to generate CF3 radicals and proceeds through a polarity-reversal cascade strategy employing electron-rich alkenes as linkers. A broad range of alkenes and heterocycles was evaluated, and the chemo-and regioselectivity of the process were thoroughly investigated. Furthermore, mechanistic studies revealed that multiple pathways contribute to the formation of the desired products.
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BibTeX
@misc{cabreraafonso2026photocatalystfree,
title = {{Photocatalyst-Free Visible-Light-Induced Trifluoroalkylation of Electron-Deficient Heteroaromatics via a Three-Component Minisci-Type Reaction.}},
author = {María Jesús Cabrera-Afonso and Marcos Escolano and Irene García and María Sánchez-Roselló and Carlos del Pozo},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15010758/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010758/v1},
note = {CC BY-NC-ND},
}
RIS
TY - UNPB
TI - Photocatalyst-Free Visible-Light-Induced Trifluoroalkylation of Electron-Deficient Heteroaromatics via a Three-Component Minisci-Type Reaction.
AU - María Jesús Cabrera-Afonso
AU - Marcos Escolano
AU - Irene García
AU - María Sánchez-Roselló
AU - Carlos del Pozo
PY - 2026
DA - 2026/10/21
PB - ChemRxiv
DO - 10.26434/chemrxiv.15010758/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010758/v1
AB - The combination of electron-poor heterocycles and trifluoromethyl motifs is widely found in pharmaceuticals, making the development of methods for the simultaneous introduction of these two features highly desirable. Herein, we report a fast, acid-free, metal-free, photocatalyst-free, and operationally simple multicomponent approach for the trifluoroalkylation of electron-poor heterocycles under open-air conditions. The method relies on the ability of trifluoromethyl thianthrenium triflate to generate CF3 radicals and proceeds through a polarity-reversal cascade strategy employing electron-rich alkenes as linkers. A broad range of alkenes and heterocycles was evaluated, and the chemo-and regioselectivity of the process were thoroughly investigated. Furthermore, mechanistic studies revealed that multiple pathways contribute to the formation of the desired products.
ER -