ChemInform Abstract: Rhodium(II)-Catalyzed CH Insertions with (((4-Nitrophenyl)sulfonyl) imino)phenyl-λ3-iodane.

✍ Scribed by I. NAEGELI; C. BAUD; G. BERNARDINELLI; Y. JACQUIER; M. MORAN; P. MUELLER

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 31 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199739035

✦ Synopsis

Rhodium(II)-Catalyzed

CH Insertions with (((4-Nitrophenyl)sulfonyl) imino)phenyl-λ3-iodane.

-The Rh-acetate catalyzed decomposition of the title compound (II) results in formal insertion into C-H bonds, activated by phenyl or vinyl groups, or by O-substituents. Yields are enhanced by electron-releasing substituents and decreased by steric hindrance. Aziridination competes with allylic insertion. The insertion is consistent with a direct nitrene insertion mechanism, no evidence for a two-step radical process is found. The insertion reaction proceeds with retention of configuration.

-(NAEGELI, I.;