Rhodium(II)-catalyzed transylidation of aryliodonium ylides: electronic effects of aryl groups determine their thermodynamic stabilities.
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.
Ochiai
Masahito
M
Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph.tokushima-u.ac.jp
Okada
Takuya
T
Tada
Norihiro
N
Yoshimura
Akira
A
D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013816:Thermodynamics
D006847:Hydrocarbons, Iodinated; D012238:Rhodium