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Rh 2 (II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides

2011; American Chemical Society; Volume: 133; Issue: 13 Linguagem: Inglês

10.1021/ja111060q

1943-2984

Benjamin J. Stokes, Sheng Liu, Tom G. Driver,

Asymmetric Hydrogenation and Catalysis

Rhodium carboxylate complexes (1 mol %) catalyze the migration of electron-withdrawing groups to selectively produce 3-substituted indoles from β-substituted styryl azides. The relative order of migratorial aptitude for this transformation is ester ≪ amide < H < sulfonyl < benzoyl ≪ nitro.