• 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

铜催化的异酰胺与杂环卡宾硼烷的自由基选择性硼氢化反应。

Copper-catalyzed radical -selective hydroboration of ynamides with -heterocyclic carbene boranes.

作者信息

Wang Kefeng, Yu Qingzhen, Mao Wenli, Zheng Yuxin, Xu Jing, Wang Yukun

机构信息

Department of Pharmacology, School of Medicine, Southern University of Science and Technology, Shenzhen 518055, China.

Clinical Medical Research Center, Southern University of Science and Technology Hospital, Shenzhen 518055, China.

出版信息

iScience. 2022 Aug 17;25(9):104977. doi: 10.1016/j.isci.2022.104977. eCollection 2022 Sep 16.

DOI:10.1016/j.isci.2022.104977
PMID:36065185
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9440302/
Abstract

Vinylboron compounds are important compounds in organic chemistry and biology. In this communication, we developed a copper(I)-catalyzed, highly regio- and stereoselective radical -hydroboration of ynamides with -heterocyclic carbene (NHC)-ligated borane is reported, which leads to a series of -boryl enmides that can be conveniently transformed into various multi-substituted enamides. Further investigation showcased that our method is robust and scalable. The mechanism of this unique reaction is studied and discussed.

摘要

乙烯基硼化合物是有机化学和生物学中的重要化合物。在本通讯中,我们报道了一种铜(I)催化的、高度区域和立体选择性的烯酰胺与氮杂环卡宾(NHC)连接的硼烷的自由基硼氢化反应,该反应生成了一系列β-硼基烯酰胺,它们可以方便地转化为各种多取代烯酰胺。进一步的研究表明,我们的方法具有稳健性和可扩展性。对这一独特反应的机理进行了研究和讨论。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50cf/9440302/ba908fec612d/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50cf/9440302/cdd393159bc3/fx1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50cf/9440302/ba908fec612d/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50cf/9440302/cdd393159bc3/fx1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50cf/9440302/ba908fec612d/sc1.jpg

相似文献

1
Copper-catalyzed radical -selective hydroboration of ynamides with -heterocyclic carbene boranes.铜催化的异酰胺与杂环卡宾硼烷的自由基选择性硼氢化反应。
iScience. 2022 Aug 17;25(9):104977. doi: 10.1016/j.isci.2022.104977. eCollection 2022 Sep 16.
2
Radical trans-Hydroboration of Alkynes with N-Heterocyclic Carbene Boranes.氮杂环卡宾硼烷对炔烃的自由基反式硼氢化反应
Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9485-9490. doi: 10.1002/anie.201804515. Epub 2018 Jun 25.
3
Radical -Hydroboration of Substituted 1,3-Diynes with an -Heterocyclic Carbene Borane.用α-杂环卡宾硼烷对取代的1,3 -二炔进行自由基硼氢化反应
Org Lett. 2021 Feb 5;23(3):1071-1075. doi: 10.1021/acs.orglett.0c04284. Epub 2021 Jan 22.
4
1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N-Heterocyclic Carbene Boranes.N-杂环卡宾硼烷对缺电子芳环的 1,4-硼氢化反应。
J Am Chem Soc. 2020 Apr 1;142(13):6261-6267. doi: 10.1021/jacs.0c00490. Epub 2020 Mar 23.
5
Hydroboration of arynes with N-heterocyclic carbene boranes.芳炔的硼氢化反应与 N-杂环卡宾硼烷。
Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13150-4. doi: 10.1002/anie.201408345. Epub 2014 Oct 24.
6
Facile Synthesis of α-N-Heterocyclic Carbene-Boryl Ketones from N-Heterocyclic Carbene-Boranes and Alkenyl Triflates.α-杂环碳烯-硼酰基酮的简便合成:由 N-杂环碳烯-硼烷和烯基三氟甲磺酸酯出发。
J Am Chem Soc. 2019 Aug 7;141(31):12355-12361. doi: 10.1021/jacs.9b05547. Epub 2019 Jul 23.
7
Revisiting Polyfluoroarenes as Radical Acceptors: Radical C-F Bond Borylation of Polyfluoroarenes with N-Heterocyclic Carbene Boranes and Synthesis of Borane-Containing Liquid Crystals.重新审视多氟芳烃作为自由基受体:多氟芳烃与氮杂环卡宾硼烷的自由基碳-氟键硼化反应及含硼液晶的合成
Org Lett. 2020 Mar 6;22(5):2054-2059. doi: 10.1021/acs.orglett.0c00481. Epub 2020 Feb 25.
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
N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters.N-杂环卡宾硼酸碘化物催化 N-杂环卡宾硼烷和重氮酯的插入反应。
Org Lett. 2017 Jul 7;19(13):3680-3683. doi: 10.1021/acs.orglett.7b01777. Epub 2017 Jun 22.
10
Radical Reactions of N-Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles.N-杂环卡宾硼烷与有机腈的自由基反应:NHC-硼烷的氰化和丙二腈的还原脱氰。
J Am Chem Soc. 2015 Jul 8;137(26):8617-22. doi: 10.1021/jacs.5b04677. Epub 2015 Jun 23.

引用本文的文献

1
Selective multifunctionalization of -heterocyclic carbene boranes the intermediacy of boron-centered radicals.-杂环卡宾硼烷的选择性多功能化——以硼中心自由基为中间体。
Chem Sci. 2023 May 18;14(23):6341-6347. doi: 10.1039/d3sc01132a. eCollection 2023 Jun 14.

本文引用的文献

1
Olefin Functionalization/Isomerization Enables Stereoselective Alkene Synthesis.烯烃官能团化/异构化实现立体选择性烯烃合成。
Nat Catal. 2021 Aug;4(8):674-683. doi: 10.1038/s41929-021-00658-2. Epub 2021 Jul 29.
2
Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes.近年来铜催化的涉及自由基的烯烃不对称 1,2-双官能化反应的进展。
Chem Soc Rev. 2020 Jan 2;49(1):32-48. doi: 10.1039/c9cs00681h.
3
Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.
铜催化不饱和α-溴代羰基化合物与烯炔醛的串联环化反应:一种从醛简便合成酮的方法。
Chem Sci. 2016 Jul 1;7(7):4134-4139. doi: 10.1039/c5sc04980f. Epub 2016 Mar 4.
4
Highly selective catalytic -hydroboration of alkynes mediated by borenium cations and B(CF).由硼鎓阳离子和B(CF)介导的炔烃的高选择性催化硼氢化反应
Chem Sci. 2016 May 1;7(5):3384-3389. doi: 10.1039/c5sc04798f. Epub 2016 Feb 12.
5
Radical trans-Hydroboration of Alkynes with N-Heterocyclic Carbene Boranes.氮杂环卡宾硼烷对炔烃的自由基反式硼氢化反应
Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9485-9490. doi: 10.1002/anie.201804515. Epub 2018 Jun 25.
6
Ketenimines Generated from Ynamides: Versatile Building Blocks for Nitrogen-Containing Scaffolds.由烯酰胺生成的酮亚胺:含氮骨架的多功能构建模块。
Chemistry. 2018 Feb 16;24(10):2297-2304. doi: 10.1002/chem.201704689. Epub 2017 Dec 14.
7
Recent progress towards gold-catalyzed synthesis of N-containing tricyclic compounds based on ynamides.基于烯酰胺的金催化含氮三环化合物合成的最新进展。
Org Biomol Chem. 2016 Oct 12;14(40):9456-9465. doi: 10.1039/c6ob01774f.
8
Pd-Catalyzed Hydroborylation of Alkynes: A Ligand Controlled Regioselectivity Switch for the Synthesis of α- or β-Vinylboronates.钯催化的炔烃硼氢化反应:用于合成α-或β-乙烯基硼酸酯的配体控制区域选择性开关
Org Lett. 2016 Feb 5;18(3):432-5. doi: 10.1021/acs.orglett.5b03416. Epub 2016 Jan 13.
9
Synthesis of 1,3-Dialkylimidazol-2-ylidene Boranes from 1,3-Dialkylimidazolium Iodides and Sodium Borohydride.
J Org Chem. 2015 Oct 2;80(19):9794-7. doi: 10.1021/acs.joc.5b01682. Epub 2015 Sep 30.
10
Copper-Catalyzed Radical/Radical C(sp 3)-H/P-H Cross-Coupling: α-Phosphorylation of Aryl Ketone O-Acetyloximes.铜催化的自由基/自由基 C(sp3)-H/P-H 交叉偶联:芳基酮 O-乙酰氧基肟的 α-磷酸化。
Angew Chem Int Ed Engl. 2015 May 26;54(22):6604-7. doi: 10.1002/anie.201501287. Epub 2015 Apr 8.