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Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

ABSTRACT: A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.

SUBMITTER: Liao J 

PROVIDER: S-EPMC6517243 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

Liao Jennie J   Basch Corey H CH   Hoerrner Megan E ME   Talley Michael R MR   Boscoe Brian P BP   Tucker Joseph W JW   Garnsey Michelle R MR   Watson Mary P MP  

Organic letters 20190327 8

A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction. ...[more]

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