38602-84-5Relevant 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
, p. 10797 - 10815 (2009)
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.
Regioselective bipyrrole coupling of pyrroles and 3-substituted pyrroles using phenyliodine(III) bis(trifluoroacetate)
Dohi, Toshifumi,Morimoto, Koji,Ito, Motoki,Kita, Yasuyuki
, p. 2913 - 2919 (2008/03/13)
A series of electron-rich bipyrroles were prepared by the regioselective, phenyliodine(III) bis(trifluoroacetate) (PIFA) induced oxidative coupling of pyrroles in the presence of bromotrimethylsilane. Using pyrrole and 3,4-disubstituted pyrroles gave exclusively 2,2′-linked bipyrroles without the formation of other bipyrrole regioisomers. The 3-alkyl- or 3-aryl-substituted pyrroles gave unsymmetrical H-T dimers in high yields as the major isolable α-linked bipyrrole products over the symmetrical H-H dimers. The nature of the N-substituent significantly influences the regioselectivity of the reaction, thus regiocontrolled bipyrrole coupling of N-phenyl- and N-benzyl-substituted pyrroles gave 2,3′-bipyrroles. Georg Thieme Verlag Stuttgart.
