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Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate.

Organic letters (2005-06-17)
Arthur J Catino, Jason M Nichols, Raymond E Forslund, Michael P Doyle
ABSTRACT

[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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
p-Toluenesulfonamide, ReagentPlus®, ≥99%