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

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journal contribution
posted on 13.12.2019, 20:05 by Hong-Gang Cheng, Maoping Pu, Gourab Kundu, Franziska Schoenebeck
We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation–deprotonation as the preferred reaction pathway.