Samarium(II)-mediated spirocyclization by intramolecular aryl radical addition onto an aromatic ring
Samarium(II)-mediated spirocyclization by intramolecular aryl radical addition onto an aromatic ring
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DOI：
10.1021/jo800656a
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发表时间：
2008-09-19
影响因子：
3.6
通讯作者：
Tanaka, Tetsuaki
中科院分区：
文献类型：
--
作者：
Iwasaki, Hiroki;Eguchi, Toru;Tanaka, Tetsuaki
在HMPA的作用下，N-（2-碘苯基）-N-烷基苯酰胺与sm2反应，生成了螺旋环吲哚啉-2- 1衍生物，从而实现了钐（II）介导的芳环上芳基自由基分子内加成的螺旋环化。通过芳基自由基加成到苯环上而不含吸电子基团，醚同源物以中等产率提供螺环苯并呋喃衍生物。还描述了与其他芳基如萘和吲哚环的反应。
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.