Templ, J., & Schnürch, M. (2023, June 19). Unlocking Monoselective N-Methylation with Quaternary Ammonium Salts [Conference Presentation]. XLVII “A. Corbella” International Summer School on Organic Synthesis 2023, Gargnano, Italy.
We herein report the use of phenyl trimethylammonium iodide (PhMe3NI) as a safe, nontoxic, and easy-to-handle reagent for an absolutely monoselective N-methylation of amides and related compounds as well as for the N-methylation of indoles. In addition, we expanded the method to N-ethylation using PhEt3NI. The ease of operational setup, high yields of ≤99%, high functional group tolerance, and especially the excellent monoselectivity for amides make this method attractive for late-stage methylation of bioactive compounds.
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Project title:
Substitution von gasförmigen Reagenzien durch Feststoffe: P 33064-N (FWF - Österr. Wissenschaftsfonds)
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Research Areas:
Biological and Bioactive Materials: 20% Beyond TUW-research foci: 80%
