- Hypervalent iodine-induced nucleophilic substitution of para-substituted phenol ethers. Generation of cation radicals as reactive intermediates
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A novel hypervalent iodine induced nucleophilic substitution of para-substituted phenol ethers in the presence of a variety of nucleophiles is described. UV and ESR spectroscopic studies indicate that this reaction proceeds via cation radicals, [ArH?+], as reactive intermediates generated by single-electron transfer (SET) from a charge-transfer (CT) complex of phenol ethers with phenyliodine(III) bis(trifluoroacetate) (PIFA). This is the first case that involves a radical intermediate on hypervalent iodine oxidations of aromatic compounds.
- Kita, Yasuyuki,Tohma, Hirofumi,Hatanaka, Kenji,Takada, Takeshi,Fujita, Shigekazu,Mitoh, Shizue,Sakurai, Hiromu,Oka, Shigenori
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p. 3684 - 3691
(2007/10/02)
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- A novel oxidative azidation of aromatic compounds with hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl azide
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A novel and useful method for the azidation of aromatic compounds by the reaction of hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) in 1,1,1,3,3,3-hexafluoro-2-propanol followed by treatment of trimethylsilyl azide (TMSA) was developed. The possible mechanism is also discussed.
- Kita,Tohma,Inagaki,Hatanaka,Yakura
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p. 4321 - 4324
(2007/10/02)
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