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Yttrium-Catalyzed Addition of Benzylic C[BOND]H Bonds of Alkyl Pyridines to Olefins

Authors

  • Dr. Bing-Tao Guan,

    1. Organometallic Chemistry Laboratory and Advanced Catalyst Research Team, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
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  • Dr. Baoli Wang,

    1. Organometallic Chemistry Laboratory and Advanced Catalyst Research Team, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
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  • Dr. Masayoshi Nishiura,

    1. Organometallic Chemistry Laboratory and Advanced Catalyst Research Team, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
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  • Prof. Dr. Zhaomin Hou

    Corresponding author
    1. Organometallic Chemistry Laboratory and Advanced Catalyst Research Team, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
    • Organometallic Chemistry Laboratory and Advanced Catalyst Research Team, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)===

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  • This work was partly supported by a Grant-in-Aid for Scientific Research (S) (21225004) from JSPS and the Key Project of International Cooperation of NSFC (20920102030). Dr. Jianhua Cheng and Dr. Masanori Takimoto are gratefully appreciated for helpful discussions.

Abstract

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Cationic half-sandwich yttrium alkyl complexes catalyze the ortho-selective benzylic C[BOND]H addition of dialkyl pyridines to various olefins, such as ethylene, 1-hexene, styrenes, and 1,3-conjugated dienes, to afford new alkylated and allylated pyridine derivatives (see scheme; Cp=C5Me5). A cationic half-sandwich yttrium picolyl species, such as [CpY(2-CH2-6-CH3C5H3N)]+, has been confirmed to be a key active species in this transformation.

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