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. 2008 Sep 19;73(18):7145-52.
doi: 10.1021/jo800656a. Epub 2008 Aug 13.

Samarium(II)-mediated spirocyclization by intramolecular aryl radical addition onto an aromatic ring

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Samarium(II)-mediated spirocyclization by intramolecular aryl radical addition onto an aromatic ring

Hiroki Iwasaki et al. J Org Chem. .

Abstract

Samarium(II)-mediated spirocyclization by intramolecular addition of aryl radicals onto an aromatic ring was achieved by the reaction of N-(2-iodophenyl)-N-alkylbenzamides with SmI2 in the presence of HMPA, yielding spirocyclic indolin-2-one derivatives. The ether congeners afford spirocyclic benzofuran derivatives in moderate yields by aryl radical addition onto a benzene ring without having an electron-withdrawing group. The reaction with other aryl groups such as naphthalene and indole rings is also described.

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