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Letter

Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate

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Arthur J. Catino, Jason M. Nichols, Raymond E. Forslund, and Michael P. Doyle*

Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742

Org. Lett., 2005, 7 (13), pp 2787–2790

DOI: 10.1021/ol0510973

Publication Date (Web): May 26, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mdoyle3@umd.edu

Abstract

A mild, efficient, and selective aziridination of olefins catalyzed by dirhodium(II) caprolactamate [Rh₂(cap)₄·2CH₃CN] is described. Use of p-toluenesulfonamide (TsNH₂), 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 % Rh₂(cap)₄. Aziridine formation occurs through Rh₂⁵⁺-catalyzed aminobromination and subsequent base-induced ring closure. An X-ray crystal structure of a Rh₂⁵⁺ halide complex, formed from the reaction between Rh₂(cap)₄ and N-chlorosuccinimide, has been obtained.

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Published In Issue June 23, 2005
Received May 11, 2005

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Letter

Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate

Abstract

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History

Recommend & Share

Related Content

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