title: Samarium(II)-mediated spirocyclization by intramolecular aryl radical addition onto an aromatic ring.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Iwasaki
authors.forename: Toru
authors.initials: T
authors.lastname: Eguchi
authors.forename: Nozomi
authors.initials: N
authors.lastname: Tsutsui
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
authors.forename: Tetsuaki
authors.initials: T
authors.lastname: Tanaka
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001549:Benzamides; D005609:Free Radicals; D007211:Indoles; D007454:Iodides; D013141:Spiro Compounds; C456900:indolin-2-one; D012493:Samarium; C409809:samarium diiodide