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Synlett 2011(17): 2513-2516  
DOI: 10.1055/s-0030-1260338
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Catalyzed Ring-Opening of meso-Aziridines with Amines

Alex Marti, Luise Richter, Christoph Schneider*
Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: schneider@chemie.uni-leipzig.de;
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Publication History

Received 19 August 2011
Publication Date:
27 September 2011 (online)

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Abstract

A cationic iron complex has been found to catalyze the aminolysis of meso-N-aryl aziridines very efficiently furnishing valuable 1,2-diamines in typically excellent yields. This protocol is compatible with a range of functional groups both in the aziridine and amine components.

Key words

amine - aziridine - catalysis - 1,2-diamine - iron

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12

General Procedure for the Iron-Catalyzed Ring-Opening of meso -Aziridines with Amines
FeCl2(mep) (24 mg, 0.05 mmol, 5 mol%) was dissolved in CH2Cl2 (2 mL) and mixed with AgSbF6 (34 mg, 0.10 mmol, 10 mol%), under an argon atmosphere, for 30 min at r.t. Subsequently, a solution of the aniline (1.20 mmol) in CH2Cl2 (1 mL) was added followed by a solution of the respective aziridine (1.00 mmol) in CH2Cl2 (1 mL). Stirring was continued at r.t. until the reaction was judged complete by GC analysis. The GC yields were determined against iodobenzene as internal standard. The solvents were removed under nitrogen flux, and the crude product was purified with chromatography over silica gel using pentane-EtOAc (30:1) as eluent. For analytical and spectroscopic details of the products, see ref. 3.