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Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from ?-nitro styryl azides.

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

SUBMITTER: Stokes BJ

PROVIDER: S-EPMC3082431 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides.

Stokes Benjamin J BJ Liu Sheng S Driver Tom G TG

Journal of the American Chemical Society 20110314 13

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. ...[more]

PMID: 21401042

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