30697-09-7Relevant academic research and scientific papers
Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent
Dohi, Toshifumi,Ito, Motoki,Yamaoka, Nobutaka,Morimoto, Koji,Fujioka, Hiromichi,Kita, Yasuyuki
experimental part, p. 10797 - 10815 (2010/03/01)
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.
Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane
Dohi, Toshifumi,Morimoto, Koji,Maruyama, Akinobu,Kita, Yasuyuki
, p. 2007 - 2010 (2007/10/03)
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.
Electrophilic substitution reactions of indoles: Part XVI-An interesting trimerisation of 3-methylindole (skatole) via Plancher rearrangement
Banerji, J.,Saha, M.,Kanrar, S.,Mukherjee, P.
, p. 1095 - 1097 (2007/10/03)
A new indole trimer 1 has been synthesised by the electrophilic substitution of 3-methylindole via a double Plancher rearrangement.
