Efficient N-methylation of primary amides using methanol under Mn(I)-catalysis

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Reshma Babu , Smruti Rekha Padhy , Ekambaram Balaraman
{"title":"Efficient N-methylation of primary amides using methanol under Mn(I)-catalysis","authors":"Reshma Babu ,&nbsp;Smruti Rekha Padhy ,&nbsp;Ekambaram Balaraman","doi":"10.1016/j.tet.2025.134535","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we report the use of methanol, a renewable, cost-effective, and easily handled reagent, for the highly selective <em>N</em>-methylation of amides under mild conditions. The reaction is catalyzed by a well-defined Mn-PNP pincer complex and proceeds <em>via</em> the borrowing hydrogen strategy (BHS). This method exhibits broad functional group tolerance and utilizes methanol as a methylating agent, demonstrating exceptional monoselectivity for amides, which enhances its practical appeal. Additionally, a series of control experiments were conducted to provide deeper mechanistic insights into the transformation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134535"},"PeriodicalIF":2.1000,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025000912","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

Herein, we report the use of methanol, a renewable, cost-effective, and easily handled reagent, for the highly selective N-methylation of amides under mild conditions. The reaction is catalyzed by a well-defined Mn-PNP pincer complex and proceeds via the borrowing hydrogen strategy (BHS). This method exhibits broad functional group tolerance and utilizes methanol as a methylating agent, demonstrating exceptional monoselectivity for amides, which enhances its practical appeal. Additionally, a series of control experiments were conducted to provide deeper mechanistic insights into the transformation.

Abstract Image

求助全文
约1分钟内获得全文 求助全文
来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信