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Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride

Hong-Gang Cheng, Maoping Pu, Gourab Kundu and Franziska Schoenebeck*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Email:

H.-G. Cheng, M. Pu, G. Kundu, F. Schoenebeck, Org. Lett., 2020, 22, 331-334.

DOI: 10.1021/acs.orglett.9b04400 (free Supporting Information)

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Tetramethylammonium fluoride (TMAF) enables a direct and selective methylation of various amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification.

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Key Words

Amides, Indoles, N-alkylation of heterocycles

ID: J54-Y2020