Deaminative Reductive Methylation of Alkylpyridinium Salts
- 31 August 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7059-7063
- https://doi.org/10.1021/acs.orglett.1c02458
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.Keywords
Funding Information
- Division of Chemistry (CHE0421224, CHE0840401, CHE1048367, CHE1229234)
- NIH Office of the Director (S10 OD016267)
- National Institute of General Medical Sciences (P20 GM103541, P20 GM104316, R35 GM131816)
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