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Keywords = Langlois reagent

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14 pages, 1209 KB  
Article
Cu(II)-Catalyzed Oxidative Trifluoromethylation of Indoles with KF as the Base
by Xiaolin Shi, Xiaowei Li, Lina Ma and Dayong Shi
Catalysts 2019, 9(3), 278; https://doi.org/10.3390/catal9030278 - 19 Mar 2019
Cited by 24 | Viewed by 5051
Abstract
This paper offers an efficient copper-catalyzed oxidative trifluoromethylation of indoles with low-cost CF3SO2Na via C–H activation. Notably, the use of a base is crucial for the trifluoromethylation of indoles. This reaction proceeds efficiently in good to excellent yields and [...] Read more.
This paper offers an efficient copper-catalyzed oxidative trifluoromethylation of indoles with low-cost CF3SO2Na via C–H activation. Notably, the use of a base is crucial for the trifluoromethylation of indoles. This reaction proceeds efficiently in good to excellent yields and is tolerance of a broad range of functional groups. Furthermore, melatonin, a medicine for sleep disorders, is converted to its 2-CF3 analogue in 68% yield. Studies of possible reaction pathways suggest that this reaction proceeds through a radical process. Full article
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12 pages, 3195 KB  
Article
Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
by Alex Abramov, Hendrik Vernickel, César Saldías and David Díaz Díaz
Molecules 2019, 24(1), 29; https://doi.org/10.3390/molecules24010029 - 21 Dec 2018
Cited by 8 | Viewed by 4999
Abstract
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 (CF3 [...] Read more.
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. Full article
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