Overcoming the Challenges towards Selective C(6)-H Alkylation of 2-Pyridone with Maleimide through Mn(I)-Catalyst: Migration of directing group through cleavage of C-N bond for the formation of all-carbon quaternary carbon center

Smruti Ranjan Mohanty, Namrata Prusty, S. Banjare, Tanmayee Nanda, P. Ravikumar
{"title":"Overcoming the Challenges towards Selective C(6)-H Alkylation of 2-Pyridone with Maleimide through Mn(I)-Catalyst: Migration of directing group through cleavage of C-N bond for the formation of all-carbon quaternary carbon center","authors":"Smruti Ranjan Mohanty, Namrata Prusty, S. Banjare, Tanmayee Nanda, P. Ravikumar","doi":"10.33774/chemrxiv-2021-jf8r2-v2","DOIUrl":null,"url":null,"abstract":"An earth-abundant and inexpensive Mn(I)-catalyzed alkylation of 2-pyridone with maleimide has been reported for the first time, in contrast to previously reported Diels-alder product. The directing group was easily removed after functionalization. Notably, unexpected migration of pyridine ring has been discovered in presence of acetic acid, which also provides unique class of compounds with three different N-heterocycles with an all-carbon quaternary carbon center. Furthermore, single crystal X-ray and HRMS revealed a five-membered manganacycle intermediate. This methodology tolerates a wide variety of functional groups delivering the alkylated products in moderate to excellent yields.","PeriodicalId":72565,"journal":{"name":"ChemRxiv : the preprint server for chemistry","volume":" ","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2021-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemRxiv : the preprint server for chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.33774/chemrxiv-2021-jf8r2-v2","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

An earth-abundant and inexpensive Mn(I)-catalyzed alkylation of 2-pyridone with maleimide has been reported for the first time, in contrast to previously reported Diels-alder product. The directing group was easily removed after functionalization. Notably, unexpected migration of pyridine ring has been discovered in presence of acetic acid, which also provides unique class of compounds with three different N-heterocycles with an all-carbon quaternary carbon center. Furthermore, single crystal X-ray and HRMS revealed a five-membered manganacycle intermediate. This methodology tolerates a wide variety of functional groups delivering the alkylated products in moderate to excellent yields.
Mn(I)催化剂对2-吡啶酮与马来酰亚胺选择性C(6)-H烷基化反应的克服:通过C- n键断裂引导基团迁移形成全碳季碳中心
与以往报道的Diels-alder产物相比,首次报道了一种储量丰富且价格低廉的Mn(I)催化2-吡啶酮与马来酰亚胺的烷基化反应。官能化后的导向基团容易去除。值得注意的是,吡啶环在乙酸的存在下发生了意想不到的迁移,这也提供了一类独特的化合物,具有三个不同的n -杂环和一个全碳的季碳中心。此外,单晶x射线和HRMS显示了一个五元锰环中间体。这种方法适用于各种各样的官能团,以中等到优异的收率提供烷基化产品。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
自引率
0.00%
发文量
0
×
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