Palladium-Catalyzed Intermolecular Aerobic Oxidative Amination of Terminal Alkenes: Efficient Synthesis of Linear Allylamine Derivatives

O2‐coupled allylic CH amination: A first general palladium‐mediated intermolecular aerobic oxidative allylic amination was developed to synthesize linear (E)‐allylimides with high regioselectivity (see scheme; MA=maleic anhydride). The proposed mechanism involves an allylic CH activation with subs...

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Published inAngewandte Chemie International Edition Vol. 47; no. 25; pp. 4733 - 4736
Main Authors Liu, Guosheng, Yin, Guoyin, Wu, Liang
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 09.06.2008
WILEY‐VCH Verlag
Wiley
Subjects
alkenes
Alkenes - chemistry
Allylamine - analogs & derivatives
Allylamine - chemical synthesis
Allylamine - chemistry
allylic compounds
Amination
Catalysis
Chemistry
Chemistry, Multidisciplinary
Molecular Structure
oxidation
Oxidation-Reduction
Oxygen - chemistry
palladium
Palladium - chemistry
Physical Sciences
Science & Technology
1,3-DIENES
oxidation
ALLYLIC AMINATION
STYRENE
HYDROAMINATION
alkenes
PI-ALLYLPALLADIUM COMPLEXES
allylic compounds
1,4-DIACETOXYLATION
palladium
OLEFINS
amination
NUCLEOPHILIC-ATTACK
C-H AMINATION
ALKALOIDS
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Summary:O2‐coupled allylic CH amination: A first general palladium‐mediated intermolecular aerobic oxidative allylic amination was developed to synthesize linear (E)‐allylimides with high regioselectivity (see scheme; MA=maleic anhydride). The proposed mechanism involves an allylic CH activation with subsequent nitrogen nucleophile substitution. The catalytic system allows efficient dioxygen‐coupled turnover without additional cocatalysts.
Bibliography:ark:/67375/WNG-17HGLWXH-N
Chinese Academy of Sciences
We are grateful for financial support from the Chinese Academy of Sciences, the National Nature Science Foundation of China (No. 20842002) and the Science and Technology Commission of the Shanghai Municipality (Grant No. 07JC14063). G. Liu thanks Prof. Shannon S. Stahl and Prof. Xiyan Lu for helpful discussions.
National Nature Science Foundation of China - No. 20842002
Science and Technology Commission of the Shanghai Municipality - No. 07JC14063
istex:6C64F2C271171A00B3591E3F236CD5E38EE5888F
ArticleID:ANIE200801009
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.200801009