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. 2011 Apr 6;133(13):4702-5.
doi: 10.1021/ja111060q. Epub 2011 Mar 14.

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

Benjamin J Stokes  1 , Sheng Liu, Tom G Driver
Affiliations

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

Benjamin J Stokes et al. J Am Chem Soc. .

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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Figures

Scheme 1
Scheme 1
Potential Mechanism for NO2 Migration.
Scheme 2
Scheme 2
Double Crossover- and Relative Rate Experiments.
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References

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