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Catalytic Arylation of a C[BOND]H Bond in Pyridine and Related Six-Membered N-Heteroarenes Using Organozinc Reagents

Authors

  • Isao Hyodo,

    1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7396
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  • Dr. Mamoru Tobisu,

    Corresponding author
    1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7396
    2. Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7395
    • Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7396

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  • Prof. Dr. Naoto Chatani

    Corresponding author
    1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7396
    • Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7396

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Abstract

Despite significant advances in the catalytic direct arylation of heteroarenes, the application of this reaction to pyridines has been met with limited success. An oxidative nucleophilic arylation strategy has been developed to overcome this problem. Pyridine, pyrazine, quinolone, and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using the developed nickel-catalyzed reaction. This protocol serves as a complementary method to catalytic direct arylation reactions.

Abstract

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