51. Rhenium-Catalysed Trifluoromethylation of Arenas and Heteroarenes by Hypervalent Iodine Reagents
- Author
-
Antonio Togni and Esteban Mejía
- Subjects
Trifluoromethyl ,Chloroform ,010405 organic chemistry ,Trifluoromethylation ,Induction period ,Hypervalent molecule ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,Catalysis ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Reagent ,Electrophile ,Organic chemistry ,Benzene - Abstract
Methyltrioxorhenium acts as a catalyst (5 10 Mol ) for the direct electrophilic trifluoromethylation of various aromatic and heteroaromatic compounds using the hypervalent iodine reagent 1 (trifluoromethyl) 12 benziodoxol 3(1H) one (1). The products are formed in up to 77 yield. Mixtures of regioisomers are obtained in the case of substituted and heteroaromatic substrates. The reaction typically carried out in chloroform solvent at 70 degrees C shows a significant induction period. Monitoring by EPR shows the involvement of radical species. A small kinetic deuterium isotope effect of 1.3 is observed for benzene.
- Published
- 2012
- Full Text
- View/download PDF