Overcoming Selectivity Trade-Offs in Alkene Azidodifluoroalkylation: An Enlightening Synergistic Catalytic Approach

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-23 DOI:10.1021/acs.orglett.4c04015
Zhao-Juan Wu, Ziyang Li, Yue Ren, Ling-Guo Meng
{"title":"Overcoming Selectivity Trade-Offs in Alkene Azidodifluoroalkylation: An Enlightening Synergistic Catalytic Approach","authors":"Zhao-Juan Wu, Ziyang Li, Yue Ren, Ling-Guo Meng","doi":"10.1021/acs.orglett.4c04015","DOIUrl":null,"url":null,"abstract":"Recent advances in dual catalysis involving biomimetic conversion strategies that utilize radical ligand transfer (RLT) often rely on large doses of precious metal additives. The role of these additives within the mechanism remains ambiguous, leading to complex reaction conditions, uncertain pathways, and increased costs. These challenges complicate the study of the reaction process and are accompanied by potential safety risks. To address these issues, azide salt was used as an alternative to TMSN<sub>3</sub>. This replacement not only avoids the drawbacks associated with almost parallel research on alkene azidodifluoroalkylation but also eliminates the need for ligands. Comparative analysis indicates that existing biomimetic synergistic catalysis strategies require Ag<sub>2</sub>CO<sub>3</sub> additives to enhance selectivity in alkene difunctionalization reactions, highlighting the superior simplicity, environmental friendliness, and operational ease of our developed synergistic catalysis strategy. Furthermore, under the guidance of our proposed mechanism, an alkene azidosulfonation was designed, validating the innovative and practical applicability of our synergistic catalysis approach.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"6 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04015","RegionNum":1,"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

Recent advances in dual catalysis involving biomimetic conversion strategies that utilize radical ligand transfer (RLT) often rely on large doses of precious metal additives. The role of these additives within the mechanism remains ambiguous, leading to complex reaction conditions, uncertain pathways, and increased costs. These challenges complicate the study of the reaction process and are accompanied by potential safety risks. To address these issues, azide salt was used as an alternative to TMSN3. This replacement not only avoids the drawbacks associated with almost parallel research on alkene azidodifluoroalkylation but also eliminates the need for ligands. Comparative analysis indicates that existing biomimetic synergistic catalysis strategies require Ag2CO3 additives to enhance selectivity in alkene difunctionalization reactions, highlighting the superior simplicity, environmental friendliness, and operational ease of our developed synergistic catalysis strategy. Furthermore, under the guidance of our proposed mechanism, an alkene azidosulfonation was designed, validating the innovative and practical applicability of our synergistic catalysis 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
克服烯烃叠氮二氟烷基化的选择性权衡:一种具有启发性的协同催化方法
双催化的最新进展涉及利用自由基配体转移(RLT)的仿生转化策略,通常依赖于大剂量的贵金属添加剂。这些添加剂在机理中的作用仍然不明确,导致复杂的反应条件,不确定的途径和增加的成本。这些挑战使反应过程的研究复杂化,并伴随着潜在的安全风险。为了解决这些问题,叠氮化物盐被用作TMSN3的替代品。这种替代不仅避免了与几乎平行的烯叠氮二氟烷基化研究相关的缺点,而且消除了对配体的需要。对比分析表明,现有的仿生协同催化策略需要Ag2CO3添加剂来提高烯烃双官能化反应的选择性,突出了我们开发的协同催化策略的简单性、环保性和操作便捷性。此外,在我们提出的机制的指导下,设计了烯烃叠氮磺化反应,验证了我们的协同催化方法的创新性和实用性。
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
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
期刊最新文献
Exploring γ-Nitroketones as 1,4-Dicarbonyl Precursors for Annulation to Pyridazines through Interrupted Nef Reaction. Synergistic CRISPR–Cas9 Host Engineering and Enzyme Evolution for Enantioselective Synthesis of a Vibegron Pyrrolidine Intermediate Bioinspired Total Synthesis of Mulberrofurans G and J, Inethermulberrofuran C, and Mongolicin C from a Common Intermediate Visible-Light-Induced Bi2O3 Catalysis toward 2-fold gem-Difluoroalkylation of Quinoxalinones Alkoxycarbonylating Reagents from Tetrahydroquinazoline: Enabling Photoredox Catalyst-Free Construction of C(sp2)–C(sp3) and C(sp2)–C(sp2) Bonds
×
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:604180095
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