- Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent
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In 1994, we first determined the single-electron-transfer (SET) oxidation ability of phenyliodine(III) bis(trifluoroacetate) (PIFA) toward phenyl ethers, affording the corresponding aromatic cation radicals. Since then, hypervalent iodine(III) has been utilized as a selective and efficient SET oxidizing agent that enables a variety of direct C-H functionalizations of aromatic rings in electron-rich arenes under mild conditions. We have now extended the original method to work in a series of heteroaromatic compounds such as thiophenes, pyrroles, and indoles. The investigations and results obtained since the start of this century are summarized in this article.
- Dohi, Toshifumi,Ito, Motoki,Yamaoka, Nobutaka,Morimoto, Koji,Fujioka, Hiromichi,Kita, Yasuyuki
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experimental part
p. 10797 - 10815
(2010/03/01)
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- Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane
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The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), mediates the unprecedented, oxidative coupling reaction of pyrroles to give α-linked bipyrroles selectively in the presence of bromotrimethylsilane. This straightforward synthesis could provide 2,3′-bipyrrole by the choice of a N-substituent of pyrrole. Mechanistic consideration of the present reaction is also described.
- Dohi, Toshifumi,Morimoto, Koji,Maruyama, Akinobu,Kita, Yasuyuki
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p. 2007 - 2010
(2007/10/03)
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- Electrophilic substitution reactions of indoles: Part XVI-An interesting trimerisation of 3-methylindole (skatole) via Plancher rearrangement
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A new indole trimer 1 has been synthesised by the electrophilic substitution of 3-methylindole via a double Plancher rearrangement.
- Banerji, J.,Saha, M.,Kanrar, S.,Mukherjee, P.
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p. 1095 - 1097
(2007/10/03)
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