title: Rhodium(II)-catalyzed transylidation of aryliodonium ylides: electronic effects of aryl groups determine their thermodynamic stabilities.
abstract: Intermolecular transylidations between aryliodonium ylides under catalytic conditions were developed. Heating a solution of phenyliodonium bis(trifluoromethylsulfonyl)methylide in a large amount (80 equiv) of a substituted iodobenzene in the presence of 5 mol % of rhodium(II) acetate as a catalyst transfers the bis(trifluoromethylsulfonyl)-methylidene group to the iodine(I) atom and affords a substituted aryliodonium ylide in a good yield. Reversible nature of the catalytic intermolecular transylidation makes it possible to evaluate the thermodynamic stability of aryliodonium ylides.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph.tokushima-u.ac.jp
authors.forename: Masahito
authors.initials: M
authors.lastname: Ochiai
authors.forename: Takuya
authors.initials: T
authors.lastname: Okada
authors.forename: Norihiro
authors.initials: N
authors.lastname: Tada
authors.forename: Akira
authors.initials: A
authors.lastname: Yoshimura
mesh_terms: D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D006847:Hydrocarbons, Iodinated; D012238:Rhodium