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Synfacts 2008(2): 0127-0127  
DOI: 10.1055/s-2007-992457
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Copper(I)-Catalyzed Diamination of Terminal Olefins to Vicinal Diamines

Contributor(s): Victor Snieckus, Erhad Ascic
B. Zhao, W. Yuan, H. Du, Y. Shi*
Colorado State University, Fort Collins, USA
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Publikationsdatum:
23. Januar 2008 (online)

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Significance

A copper(I)-catalyzed intermolecular diamination of various conjugated terminal olefins (1) with di-tert-butylthiadiaziridine 1,1-dioxide (2) as nitrogen source, providing various diamination products (3) under mild reaction conditions is described. Deprotection of 3 as illustrated in the scheme yields a variety of vicinal diamines and unsubstituted thiadiazine 1,2-dioxides. Support for a radical mechanism for this interesting reaction using deuterated styrene as olefinic substrate was obtained.