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Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity

1
Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, Regensburg 93053, Germany
2
Departamento de Química Física, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 302, Santiago Correo 22, Chile
3
Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(1), 29; https://doi.org/10.3390/molecules24010029
Received: 5 December 2018 / Revised: 14 December 2018 / Accepted: 17 December 2018 / Published: 21 December 2018
In this work we have investigated the potential benefits of using supramolecular gel networks as reaction media to carry out air-sensitive metal-free light-induced trifluoromethylation of six-membered (hetero)arenes under aerobic conditions. This reaction was performed at room temperature (RT) using sodium triflinate (CF3SO2Na, Langlois’ reagent) as a source of radicals and diacetyl as electron donor. The effects of confinement in gel media, concentration of reactants, and type of light source on yield and product distribution were evaluated and compared to the results obtained in homogeneous solution. Four different low molecular weight (LMW) gelators were employed in this study. The results confirmed the blocking effect of the gel medium against reaction quenching by external oxygen, as well as a certain control on the kinetics and selectivity. View Full-Text
Keywords: trifluoromethylation; photoinduced reaction; chemoselectivity; supramolecular gel; confined reaction media trifluoromethylation; photoinduced reaction; chemoselectivity; supramolecular gel; confined reaction media
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MDPI and ACS Style

Abramov, A.; Vernickel, H.; Saldías, C.; Díaz Díaz, D. Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity. Molecules 2019, 24, 29. https://doi.org/10.3390/molecules24010029

AMA Style

Abramov A, Vernickel H, Saldías C, Díaz Díaz D. Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity. Molecules. 2019; 24(1):29. https://doi.org/10.3390/molecules24010029

Chicago/Turabian Style

Abramov, Alex, Hendrik Vernickel, César Saldías, and David Díaz Díaz. 2019. "Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity" Molecules 24, no. 1: 29. https://doi.org/10.3390/molecules24010029

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