title: Preparation of Heteroaromatic (Aryl)iodonium Imides as I-N Bond-Containing Hypervalent Iodine.
abstract: Hypervalent iodine(III) compounds containing iodine-nitrogen bonds are very attractive amination reagents in organic synthesis. Heteroaromatic (aryl)iodonium imides containing a iodine-nitrogen bond and a hypervalent iodine(III) atom were prepared from heteroarenes, bis(sulfon)imides and (diacetoxyiodo)arenes under mild conditions. These compounds were stable under air and in organic solvents, and could be easily purified by precipitation. X-ray crystal structure analysis indicated that the structure of N-pivaloyl indolyl(phenyl)iodonium bis(tosyl)imides and N-pivaloyl indolyl(2-butoxyphenyl)iodonium bis(tosyl)imides was a dimer with a T-shaped geometry at the iodine atom linked to an indole group and a bis(tosyl)imide by a monomer unit. Moreover, the use of substituted iodoarenes facilitated the purification of some of the heteroaromatic (aryl)iodonium imides.
authors.affiliation: Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
authors.forename: Kazuma
authors.initials: K
authors.lastname: Ishida
authors.affiliation: Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
authors.forename: Hideo
authors.initials: H
authors.lastname: Togo
authors.affiliation: Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.|Molecular Chirality Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Moriyama
keywords: I−N bond; heterocycles; imides; indoles; iodine