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

Authors

  • Guosheng Liu Prof. Dr.,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, China, Fax: (+86) 21-64166128
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  • Guoyin Yin,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, China, Fax: (+86) 21-64166128
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  • Liang Wu

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, China, Fax: (+86) 21-64166128
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  • 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.

Abstract

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O2-coupled allylic C[BOND]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[BOND]H activation with subsequent nitrogen nucleophile substitution. The catalytic system allows efficient dioxygen-coupled turnover without additional cocatalysts.

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