Palladium-Catalyzed Highly Regioselective Arylation of Allylamines with Thiophenes and Furans

Authors

  • Zhen Jiang,

    1. Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, Fax: (+86)-10-6251-6444; phone: (+86)-10-6251-1528
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  • Lingjuan Zhang,

    1. Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, Fax: (+86)-10-6251-6444; phone: (+86)-10-6251-1528
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  • Chaonan Dong,

    1. Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, Fax: (+86)-10-6251-6444; phone: (+86)-10-6251-1528
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  • Zhongzheng Cai,

    1. Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, Fax: (+86)-10-6251-6444; phone: (+86)-10-6251-1528
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  • Weijun Tang,

    1. Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K.
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  • Huanrong Li,

    1. Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, Fax: (+86)-10-6251-6444; phone: (+86)-10-6251-1528
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  • Lijin Xu,

    Corresponding author
    1. Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, Fax: (+86)-10-6251-6444; phone: (+86)-10-6251-1528
    • Department of Chemistry, Renmin University of China, Beijing 100872, People's Republic of China, Fax: (+86)-10-6251-6444; phone: (+86)-10-6251-1528
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  • Jianliang Xiao

    1. Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K.
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Abstract

A palladium-catalyzed highly regioselective and stereoselective direct arylation of allylamine derivatives with a wide range of thiophenes and furans has been developed. In the presence of palladium(II) acetate [Pd(OAc)2] catalyst and appropriate oxidants, the coupling reaction proceeded with excellent group compatibility and high efficiency, leading exclusively to γ-arylated linear (E)-allylamines. It was found that the choice of solvent, olefin substrate and oxidant had an important influence on reaction efficiency, and the use of sterically demanding N,N-diprotected allylamines bearing a carbamate moiety is crucial for securing high regioselectivity and stereoslectivity. This method provides a straightforward approach for the efficient synthesis of various γ-heteroarylated, linear (E)-allylamines.

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