Samarium(II)-Mediated Spirocyclization by Intramolecular Aryl Radical Addition onto an Aromatic Ring

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 benzof...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-09, Vol.73 (18), p.7145-7152
Main Authors: Iwasaki, Hiroki, Eguchi, Toru, Tsutsui, Nozomi, Ohno, Hiroaki, Tanaka, Tetsuaki
Format: Article
Language:English
Subjects:
Benzamides - chemistry
Chemistry
Cyclization
Exact sciences and technology
Free Radicals - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles - chemical synthesis
Indoles - chemistry
Iodides - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Samarium - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800656a