Tetrahedron Letters

Desulfonyloxyiodination of arenesulfonic acids with mCPBA and molecular iodine

Y Suzuki, Y Ishiwata, K Moriyama, H Togo

Index: Suzuki, Yuhsuke; Ishiwata, Yoshihide; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron Letters, 2010 , vol. 51, # 45 p. 5950 - 5953

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Citation Number: 9

Abstract

Treatment of p-alkylbenzenesulfonic acids with mCPBA and molecular iodine gave p- alkyliodobenzenes in good to moderate yields via electrophilic ipso-substitution by the iodonium species (I+) formed. This desulfonyloxyiodination was promoted by the addition of a catalytic amount of iodoarenes, such as o-iodobenzoic acid. The same treatment of dimethylbenzenesulfonic acids and trimethylbenzenesulfonic acids with mCPBA and ...

~38%

~57%

~63%

~70%

~22%

~82%

~7%

~59%

~45%

~83%

~31%

~89%

~63%

~17%

~66%

~47%

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