Annulative Coupling of Sulfoxonium Ylides with Aldehydes and Naphthols or Coumarins: Easy Access to Fused Dihydrofurans

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-01-17 DOI:10.1021/acs.joc.4c02787
Rahul Kumar Saini, Paran J. Borpatra, Satyendra Kumar Pandey
{"title":"Annulative Coupling of Sulfoxonium Ylides with Aldehydes and Naphthols or Coumarins: Easy Access to Fused Dihydrofurans","authors":"Rahul Kumar Saini, Paran J. Borpatra, Satyendra Kumar Pandey","doi":"10.1021/acs.joc.4c02787","DOIUrl":null,"url":null,"abstract":"We present a novel, metal- and additive-free method for the robust synthesis of dihydrofuran-fused naphthalenes and coumarins. This approach utilizes the annulative coupling of sulfoxonium ylides with aldehydes, naphthols, or coumarins at ambient temperature. The method exhibits broad substrate compatibility, accommodating various functional groups on sulfoxonium ylides and naphthol or coumarin derivatives and resulting in good to high yields of the desired products. Additionally, we successfully scaled up the reactions, and the synthesized derivatives were further converted to other valuable bioactive molecules, validating the viability of our approach.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02787","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

We present a novel, metal- and additive-free method for the robust synthesis of dihydrofuran-fused naphthalenes and coumarins. This approach utilizes the annulative coupling of sulfoxonium ylides with aldehydes, naphthols, or coumarins at ambient temperature. The method exhibits broad substrate compatibility, accommodating various functional groups on sulfoxonium ylides and naphthol or coumarin derivatives and resulting in good to high yields of the desired products. Additionally, we successfully scaled up the reactions, and the synthesized derivatives were further converted to other valuable bioactive molecules, validating the viability of our approach.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
酰基亚砜与醛、萘酚或香豆素的环结偶联:容易得到融合二氢呋喃
我们提出了一种新颖的、不含金属和添加剂的方法,用于强效合成二氢呋喃融合萘和香豆素。这种方法利用了环氧磺酰基与醛、萘酚或香豆素在常温下的环状偶联。该方法具有广泛的底物兼容性,可以在锍酰化物和萘酚或香豆素衍生物上实现各种官能团的偶联,并能获得高产率的所需产物。此外,我们还成功地扩大了反应规模,合成的衍生物被进一步转化为其他有价值的生物活性分子,从而验证了我们方法的可行性。
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 去求助
来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
期刊最新文献
Catalyst-Controlled, Site-Selective Functionalization of Levoglucosan Analogues Mediated by Chiral Zinc Diamine Complexes Photooxidation and Cleavage of Ethynylated 9,10-Dimethoxyanthracenes with Acid-Labile Ether Bonds Copper-Mediated Three-Component Synthesis of Diverse Perfluoroalkylated Fullerenes Transition-Metal-Free Radical Approach for the Synthesis of Isothiocyanates by Pyridinium 1,4-Zwitterionic Thiolates as a Sulfur Source Unraveling the Mechanism and Influence of Auxiliary Ligands on the Isomerization of Neutral [P,O]-Chelated Nickel Complexes for Olefin Polymerization
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1