{"title":"Efficient N-methylation of primary amides using methanol under Mn(I)-catalysis","authors":"Reshma Babu , Smruti Rekha Padhy , 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.
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.