Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 18, Pages 7145-7152Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo800656a
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- Ministry of Education, Culture, Sports, Science and Technology of Japan
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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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