4.8 Article

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

Journal

ORGANIC LETTERS
Volume 22, Issue 1, Pages 331-334

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04400

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Funding

  1. RWTH Aachen University
  2. JARA-HPC from RWTH Aachen University [jara0091]

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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.

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