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Deaminative Reductive Methylation of Alkylpyridinium Salts.

ABSTRACT: Methyl groups can imbue valuable properties in organic molecules, often leading to enhanced bioactivity. To enable efficient installation of methyl groups on simple building blocks and in late-stage functionalization, a nickel-catalyzed reductive coupling of secondary Katritzky alkylpyridinium salts with methyl iodide was developed. When coupled with formation of the pyridinium salt from an alkyl amine, this method allows amino groups to be readily transformed to methyl groups with broad functional group and heterocycle tolerance.

SUBMITTER: Bercher OP

PROVIDER: S-EPMC8448964 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Deaminative Reductive Methylation of Alkylpyridinium Salts.

Bercher Olivia P OP Plunkett Shane S Mortimer Thomas E TE Watson Mary P MP

Organic letters 20210831 18

Methyl groups can imbue valuable properties in organic molecules, often leading to enhanced bioactivity. To enable efficient installation of methyl groups on simple building blocks and in late-stage functionalization, a nickel-catalyzed reductive coupling of secondary Katritzky alkylpyridinium salts with methyl iodide was developed. When coupled with formation of the pyridinium salt from an alkyl amine, this method allows amino groups to be readily transformed to methyl groups with broad functio ...[more]

PMID: 34464140

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