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Nickel-Catalyzed Electroreductive Coupling of Alkylpyridinium Salts and Aryl Halides.


ABSTRACT: An electrochemical, nickel-catalyzed reductive coupling of alkylpyridinium salts and aryl halides is reported. High-throughput experimentation (HTE) was employed for rapid reaction optimization and evaluation of a broad scope of pharmaceutically relevant structurally diverse aryl halides, including complex drug-like substrates. In addition, the transformation is compatible with both primary and secondary alkylpyridinium salts with distinct conditions. Mechanistic insights were critical to enhance the efficiency of coupling using secondary alkylpyridinium salts. Systematic comparisons of the electrochemical and non-electrochemical methods revealed the complementary scope and efficiency of the two approaches.

SUBMITTER: Fu J 

PROVIDER: S-EPMC10769313 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Nickel-Catalyzed Electroreductive Coupling of Alkylpyridinium Salts and Aryl Halides.

Fu Jiantao J   Lundy Windsor W   Chowdhury Rajdip R   Twitty J Cameron JC   Dinh Long P LP   Sampson Jessica J   Lam Yu-Hong YH   Sevov Christo S CS   Watson Mary P MP   Kalyani Dipannita D  

ACS catalysis 20230628 14


An electrochemical, nickel-catalyzed reductive coupling of alkylpyridinium salts and aryl halides is reported. High-throughput experimentation (HTE) was employed for rapid reaction optimization and evaluation of a broad scope of pharmaceutically relevant structurally diverse aryl halides, including complex drug-like substrates. In addition, the transformation is compatible with both primary and secondary alkylpyridinium salts with distinct conditions. Mechanistic insights were critical to enhanc  ...[more]

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