Samarium(II)-mediated spirocyclization by intramolecular aryl radical addition onto an aromatic ring |
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Authors: | Iwasaki Hiroki Eguchi Toru Tsutsui Nozomi Ohno Hiroaki Tanaka Tetsuaki |
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Affiliation: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. |
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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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