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 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.
Iwasaki
Hiroki
H
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Eguchi
Toru
T
Tsutsui
Nozomi
N
Ohno
Hiroaki
H
Tanaka
Tetsuaki
T
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
D001549:Benzamides; D005609:Free Radicals; D007211:Indoles; D007454:Iodides; D013141:Spiro Compounds; C456900:indolin-2-one; D012493:Samarium; C409809:samarium diiodide