• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

从硼代烯烃生成硼基-氮氧自由基：亚硝基烯反应

Generation of boryl-nitroxide radicals from a boraalkene the nitroso ene reaction.

作者信息

Chen Chaohuang, Daniliuc Constantin G, Klabunde Sina, Hansen Michael Ryan, Kehr Gerald, Erker Gerhard

机构信息

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster Corrensstraße 40 48149 Münster Germany

Institut für Physikalische Chemie, Westfälische Wilhelms-Universität Münster Corrensstraße 28/3040 48149 Münster Germany.

出版信息

Chem Sci. 2022 Aug 18;13(36):10891-10896. doi: 10.1039/d2sc02485c. eCollection 2022 Sep 21.

DOI:10.1039/d2sc02485c
PMID:36320693
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9491209/
Abstract

Examples of isolated boron substituted nitroxide radicals are rare. The reaction of the reactive cyclic boraalkene 3 with nitrosobenzene yields a mixture of the [2 + 2] cycloaddition product 4a, the -nitroxide radicals 5a and 6a and the azoxybenzene co-product 7a a bora nitroso ene reaction pathway, the boron analogue of the nitroso ene reaction. The products were separated by flash chromatography, and the -nitroxide radicals were characterized by X-ray diffraction and EPR spectroscopy. Radical 5a was shown to be a hydrogen atom abstractor. Both the -nitroxide radicals are more easily oxidized compared to TEMPO, as shown by cyclic voltammetry.

摘要

孤立的硼取代氮氧化物自由基的例子很少见。活性环状硼烯烃3与亚硝基苯反应生成[2 + 2]环加成产物4a、氮氧化物自由基5a和6a以及偶氮苯副产物7a的混合物，这是一条硼亚硝基烯反应途径，即亚硝基烯反应的硼类似物。产物通过快速柱色谱法分离，氮氧化物自由基通过X射线衍射和电子顺磁共振光谱进行表征。自由基5a被证明是一个氢原子提取剂。循环伏安法表明，与TEMPO相比，这两种氮氧化物自由基都更容易被氧化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/82c0e12870f0/d2sc02485c-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/ad5646625ea1/d2sc02485c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/9b4f3352244b/d2sc02485c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/87ebc73f9470/d2sc02485c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/85fb80314b05/d2sc02485c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/41783268738c/d2sc02485c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/c02ef66bdade/d2sc02485c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/938f0fafcdfe/d2sc02485c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/62b240035a43/d2sc02485c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/f0a9286dffe5/d2sc02485c-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/d96342386ecc/d2sc02485c-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/82c0e12870f0/d2sc02485c-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/ad5646625ea1/d2sc02485c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/9b4f3352244b/d2sc02485c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/87ebc73f9470/d2sc02485c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/85fb80314b05/d2sc02485c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/41783268738c/d2sc02485c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/c02ef66bdade/d2sc02485c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/938f0fafcdfe/d2sc02485c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/62b240035a43/d2sc02485c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/f0a9286dffe5/d2sc02485c-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/d96342386ecc/d2sc02485c-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e01a/9491209/82c0e12870f0/d2sc02485c-s6.jpg

相似文献

1
Generation of boryl-nitroxide radicals from a boraalkene the nitroso ene reaction.从硼代烯烃生成硼基-氮氧自由基：亚硝基烯反应
Chem Sci. 2022 Aug 18;13(36):10891-10896. doi: 10.1039/d2sc02485c. eCollection 2022 Sep 21.
2
Fast-scan voltammetry of cyclic nitroxide free radicals.环状氮氧化物自由基的快速扫描伏安法。
Anal Chem. 1996 Nov 1;68(21):3815-21. doi: 10.1021/ac960603m.
3
EPR Studies on the Addition of Ligated Boryl Radicals to Carbonyl Compounds.关于连接硼基自由基与羰基化合物加成反应的电子顺磁共振研究。
J Org Chem. 2020 Mar 20;85(6):4248-4255. doi: 10.1021/acs.joc.9b03420. Epub 2020 Feb 27.
4
N-Heterocyclic Carbene Stabilized Boryl Radicals.N-杂环卡宾稳定的硼自由基。
Angew Chem Int Ed Engl. 2017 Jan 19;56(4):1135-1140. doi: 10.1002/anie.201610903. Epub 2016 Dec 20.
5
Nitroxides scavenge myeloperoxidase-catalyzed thiyl radicals in model systems and in cells.氮氧化物在模型系统和细胞中清除髓过氧化物酶催化的硫自由基。
J Am Chem Soc. 2004 Aug 4;126(30):9221-32. doi: 10.1021/ja0495157.
6
Conversion of nitroxide radicals by phenolic and thiol antioxidants.酚类和硫醇类抗氧化剂对氮氧化物自由基的转化作用。
Free Radic Res. 1997 Jul;27(1):45-53. doi: 10.3109/10715769709097837.
7
A boron-centered radical: a potassium-crown ether stabilized boryl radical anion.一种以硼为中心的自由基：一种钾-冠醚稳定的硼基自由基阴离子。
Chem Commun (Camb). 2016 Oct 20;52(86):12714-12716. doi: 10.1039/c6cc06918e.
8
N-heterocyclic carbene boryl radicals: a new class of boron-centered radical.N-杂环卡宾硼自由基：一类新型的以硼为中心的自由基。
J Am Chem Soc. 2009 Aug 12;131(31):11256-62. doi: 10.1021/ja904103x.
9
Scavenging with TEMPO* to identify peptide- and protein-based radicals by mass spectrometry: advantages of spin scavenging over spin trapping.使用TEMPO*进行清除以通过质谱法鉴定基于肽和蛋白质的自由基：自旋清除相对于自旋捕获的优势。
J Am Chem Soc. 2003 Jul 16;125(28):8655-65. doi: 10.1021/ja0291888.
10
Electron paramagnetic resonance and computational studies of radicals derived from boron-substituted N-heterocyclic carbene boranes.硼取代的 N-杂环卡宾硼烷自由基的电子顺磁共振和计算研究。
J Am Chem Soc. 2011 Jul 6;133(26):10312-21. doi: 10.1021/ja2038485. Epub 2011 Jun 14.

本文引用的文献

1
A deprotonation pathway to reactive [B]CH boraalkenes.通往活性[B]CH硼代烯烃的去质子化途径。
Dalton Trans. 2022 May 17;51(19):7695-7704. doi: 10.1039/d2dt01193j.
2
N-Heterocyclic Carbene Stabilized 1-Bora-1,3-butadienes.N-杂环卡宾稳定的1-硼-1,3-丁二烯
J Am Chem Soc. 2021 Dec 22;143(50):21312-21320. doi: 10.1021/jacs.1c09774. Epub 2021 Dec 11.
3
Advances in chemistry of N-heterocyclic carbene boryl radicals.N-杂环卡宾硼自由基化学的进展。
Chem Soc Rev. 2021 Aug 21;50(16):8995-9021. doi: 10.1039/d1cs00385b. Epub 2021 Jul 12.
4
Formation and Cycloaddition Reactions of a Reactive Boraalkene Stabilized Internally by N-Heterocyclic Carbene.由氮杂环卡宾内部稳定的活性硼烯的形成及环加成反应
Angew Chem Int Ed Engl. 2021 Sep 1;60(36):19905-19911. doi: 10.1002/anie.202106724. Epub 2021 Aug 3.
5
Frustrated Radical Pairs: Insights from EPR Spectroscopy.受挫自由基对：电子顺磁共振波谱学的见解
Angew Chem Int Ed Engl. 2021 Jan 4;60(1):53-65. doi: 10.1002/anie.202010633. Epub 2020 Nov 17.
6
The [(NHC)B(H)C F ] Cations and Their [B](H)-CO Borane Carbonyls.[(NHC)B(H)C F ]阳离子及其[B](H)-CO硼烷羰基化合物。
Angew Chem Int Ed Engl. 2020 Nov 23;59(48):21460-21464. doi: 10.1002/anie.202009353. Epub 2020 Sep 24.
7
EPR Studies on the Addition of Ligated Boryl Radicals to Carbonyl Compounds.关于连接硼基自由基与羰基化合物加成反应的电子顺磁共振研究。
J Org Chem. 2020 Mar 20;85(6):4248-4255. doi: 10.1021/acs.joc.9b03420. Epub 2020 Feb 27.
8
Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions.四甲基哌啶氮氧自由基（TEMPO）、邻苯二甲酰亚胺氮氧自由基（PINO）及相关氮氧自由基物种：电化学性质及其在电催化反应中的应用。
Chem Rev. 2018 May 9;118(9):4834-4885. doi: 10.1021/acs.chemrev.7b00763. Epub 2018 Apr 30.
9
Voltammetric and spectroscopic study of ferrocene and hexacyanoferrate and the suitability of their redox couples as internal standards in ionic liquids.二茂铁和六氰合铁酸盐的伏安法与光谱研究及其氧化还原对作为离子液体中内标的适用性
Phys Chem Chem Phys. 2017 Nov 1;19(42):28841-28852. doi: 10.1039/c7cp05483a.
10
High-Potential Electrocatalytic O2 Reduction with Nitroxyl/NO x Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis.高电势电催化氧气还原与亚硝酰基/NOx 介体：对燃料电池和需氧氧化催化的影响。
ACS Cent Sci. 2015 Aug 26;1(5):234-43. doi: 10.1021/acscentsci.5b00163. Epub 2015 Jul 15.