Concepedia

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

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

Journal of the American Chemical Society · 2011 · 174 citations · 43 references

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Concepts

Abstract

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.

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