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Synthesis 2012(1): 27-36  
DOI: 10.1055/s-0031-1289611
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Cationic Late-Transition-Metal Complexes Catalyze the Ring Opening of Aziridines with Amines

Alex Marti, Saravanan Peruncheralathan¹, 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 20 September 2011
Publication Date:
18 November 2011 (online)

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Abstract

Cationic palladium and nickel complexes have been found to catalyze the ring-opening of meso-N-aryl aziridines with anilines very efficiently and furnish valuable 1,2-diamines in typically excellent yields. The active catalysts were generated in situ from the corresponding metal dichloride bis(triphenylphosphine) complexes through chloride abstraction with a silver salt. This new protocol is applicable across a broad substrate range with both cyclic as well as acyclic aziridines. In addition, cationic gold-phosphine complexes proved to be highly reactive as well as delivering products in comparable rates and yields.

Key words

aziridine - catalysis - 1,2-diamine - nickel - palladium

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1

Current address: National Institute of Science Education and Research, Bhubaneswar 751 005, India.