Novel and direct oxidative cyanation reactions of heteroaromatic compounds mediated by a hypervalent iodine(III) reagent.
The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) mediates the selective cyanation reactions of a wide range of electron-rich heteroaromatic compounds such as pyrroles, thiophenes, and indoles under mild conditions. These reactions proceed via a cation radical intermediate, and the key for the successful transformation presumably depends on the oxidation-reduction potential of the substrates used. The synthetic utility has been demonstrated through the conversion of these biologically important pyrroles 2f and 2g. [reaction: see text]
Dohi
Toshifumi
T
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871 Japan.
Morimoto
Koji
K
Kiyono
Yorito
Y
Tohma
Hirofumi
H
Kita
Yasuyuki
Y
D003485:Cyanates; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007202:Indicators and Reagents; D007455:Iodine; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D003485:Cyanates; D006841:Hydrocarbons, Aromatic; D007202:Indicators and Reagents; D007455:Iodine