Cu(I)-Catalyzed Regioselective Diamination of Conjugated Dienes via Dual Mechanistic Pathways

This paper describes the Cu(I)-catalyzed regioselective diamination of conjugated dienes using di-tert-butyldiaziridinone as nitrogen source. The internal diamination and terminal diamination likely proceed via two mechanistic pathways. Various dienes can be efficiently diaminated at the internal do...

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Published inJournal of the American Chemical Society Vol. 132; no. 32; pp. 11009 - 11011
Main Authors Zhao, Baoguo, Peng, Xingao, Cui, Sunliang, Shi, Yian
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.08.2010
Amer Chemical Soc
Subjects
Alkenes - chemistry
Amination
Catalysis
Chemistry
Chemistry, Multidisciplinary
Copper - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Substrate Specificity
PD-CATALYZED DIAMINATION
PROMOTED INTRAMOLECULAR DIAMINATION
ELECTROPHILIC DIAMINATION
ASYMMETRIC DIAMINATION
OXIDATIVE DIAMINATION
BOND FORMATION
CATALYZED DIAMINATION
TERMINAL OLEFINS
C-H ACTIVATION
VICINAL DIAMINATION
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ISSN0002-7863
1520-5126
1520-5126
DOI10.1021/ja103838d

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Summary:This paper describes the Cu(I)-catalyzed regioselective diamination of conjugated dienes using di-tert-butyldiaziridinone as nitrogen source. The internal diamination and terminal diamination likely proceed via two mechanistic pathways. Various dienes can be efficiently diaminated at the internal double bonds with high regio- and diasteroselectivity in good yield using inexpensive CuBr as catalyst.
Bibliography:NIH RePORTER
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja103838d