Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate
| Autor: | Michael P. Doyle, Jason M. Nichols, Raymond E. Forslund, Arthur J. Catino |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Molecular Structure
Aziridines Organic Chemistry Halide General Medicine Crystal structure Alkenes Aziridine Ring (chemistry) Biochemistry Medicinal chemistry Catalysis Potassium carbonate chemistry.chemical_compound chemistry Mixed valent Organometallic Compounds Organic chemistry Indicators and Reagents Rhodium Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 7:2787-2790 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol0510973 |
| Popis: | [reaction: see text] A mild, efficient, and selective aziridination of olefins catalyzed by dirhodium(II) caprolactamate [Rh(2)(cap)(4).2CH(3)CN] is described. Use of p-toluenesulfonamide (TsNH(2)), N-bromosuccinimide (NBS), and potassium carbonate readily affords aziridines in isolated yields of up to 95% under extremely mild conditions with as little as 0.01 mol % Rh(2)(cap)(4). Aziridine formation occurs through Rh(2)(5+)-catalyzed aminobromination and subsequent base-induced ring closure. An X-ray crystal structure of a Rh(2)(5+) halide complex, formed from the reaction between Rh(2)(cap)(4) and N-chlorosuccinimide, has been obtained. |
| Databáze: | OpenAIRE |
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