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Palladium-Catalyzed Oxidative Arylalkylation of Activated Alkenes: Dual C[BOND]H Bond Cleavage of an Arene and Acetonitrile

Authors

  • Tao Wu,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
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  • Xin Mu,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
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  • Prof. Dr. Guosheng Liu

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
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  • We are grateful for the financial support from the National Natural Science Foundation of China (20821002, 20872155, 20972175, and 20923005), the National Basic Research Program of China (973-2009CB825300), and the “Hundred Talent Project” of Chinese Academy of Science.

Abstract

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Not one but two: The title reaction proceeds through the dual C[BOND]H bond cleavage of both aniline and acetonitrile (see scheme). The reaction affords a variety of cyano-bearing indolinones in excellent yield. Mechanistic studies demonstrate that this reaction involves a fast arylation of the olefin and a rate-determining C[BOND]H activation of the acetonitrile.

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