Organic Letters 2008-01-03

Indium(III) acetate-catalyzed intermolecular radical addition of organic iodides to electron-deficient alkenes.

Katsukiyo Miura, Mitsuru Tomita, Junji Ichikawa, Akira Hosomi

Index: Org. Lett. 10(1) , 133-136, (2008)

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Abstract

In the presence of phenylsilane and a catalytic amount of indium(III) acetate, organic iodides added to electron-deficient alkenes in ethanol at room temperature. Both simple and functionalized organic iodides were applicable to this reaction. A plausible reaction mechanism involves the formation of indium hydride species by hydride transfer from silicon to indium and an indium hydride-mediated radical chain process.