Regioselective C-H Trifluoromethylation of Aromatic Compounds by Inclusion in Cyclodextrins
Xu Lu1, Ryohei Kawazu1, Jizhou Song1
1Department of Molecular and Material Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan.
Abstract:
A regioselective radical C-H trifluoromethylation of aromatic compounds was developed using cyclodextrins (CDs) as additives. The C-H trifluoromethylation proceeded with high regioselectivity to afford the product in good yield, even on the gram scale. In the presence of CDs, some substrates underwent a single trifluoromethylation selectively, whereas mixtures of single- and double-trifluoromethylated products were formed in the absence of the CD. 1H NMR experiments indicated that the regioselectivity was controlled by the inclusion of a substrate inside the CD cavity.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Frost Circles for Different Conjugated Systems
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Cycloaddition Reactions: MO Requirements for Thermal Activation
Woodward–Hoffmann Selection Rules and Microscopic Reversibility


