Work

Rh2(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides

Year: 2011

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja111060q

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

Institution: University of Illinois Chicago

Language: English

Topic: Synthesis of Indole Derivatives

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, University of Illinois at Urbana-Champaign, National Institute of General Medical Sciences

Award: N-Heterocycles from Azides through Rhodium-Catalyzed Nitrenoid Transfer