Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents

被引：16

作者：

Templ, Johanna ^{[1
]}

Gjata, Edma ^{[1
]}

Getzner, Filippa ^{[1
]}

Schnuerch, Michael ^{[1
]}

机构：

[1] TU Wien, Inst Appl Synthet Chem, A-1060 Vienna, Austria

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 40期

基金：

奥地利科学基金会;

关键词：

HETEROCYCLES; PERSPECTIVE; ALKYLATION; ALCOHOLS;

D O I：

10.1021/acs.orglett.2c02766

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：7315 / 7319

页数：5