Open AccessDeaminative Reductive Methylation of Alkylpyridinium Salts
Author(s) -
Olivia P. Bercher,
Shane Plunkett,
Thomas E. Mortimer,
Mary P. Watson
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c02458
Subject(s) - chemistry , pyridinium , alkyl , iodide , salt (chemistry) , methyl iodide , amine gas treating , combinatorial chemistry , organic chemistry , methylation , functional group , surface modification , reductive elimination , catalysis , biochemistry , gene , polymer
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.