• 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

无需外部路易斯碱作为活化剂的可见光介导的烷基硼酸烯基化反应

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator.

作者信息

Yue Fuyang, Dong Jianyang, Liu Yuxiu, Wang Qingmin

机构信息

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, People's Republic of China.

出版信息

Org Lett. 2021 Apr 2;23(7):2477-2481. doi: 10.1021/acs.orglett.1c00399. Epub 2021 Mar 12.

DOI:10.1021/acs.orglett.1c00399
PMID:33709714
Abstract

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

摘要

在此,我们报道了一种在室温下直接通过可见光介导使烷基硼酸烯基化的方法,该方法无需外部路易斯碱作为活化剂,并且我们提出了一种涉及苯亚磺酸盐对烷基硼酸进行活化的机理。该方法允许使用各种烯基砜对多种环状和非环状伯烷基硼酸和仲烷基硼酸进行高效官能化。我们通过制备或官能化几种药物和天然产物证明了其效用。

相似文献

1
Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator.无需外部路易斯碱作为活化剂的可见光介导的烷基硼酸烯基化反应
Org Lett. 2021 Apr 2;23(7):2477-2481. doi: 10.1021/acs.orglett.1c00399. Epub 2021 Mar 12.
2
Visible-light-mediated photoredox minisci C-H alkylation with alkyl boronic acids using molecular oxygen as an oxidant.利用分子氧作为氧化剂,通过可见光照介导的光氧化还原 Minisci C-H 烷基化反应,实现与烷基硼酸的反应。
Chem Commun (Camb). 2020 Oct 20;56(83):12652-12655. doi: 10.1039/d0cc05946c.
3
Visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones.可见光促进的 4-烷基-1,4-二氢吡啶与烯基砜的烷基化反应。
Org Biomol Chem. 2021 Oct 27;19(41):8924-8928. doi: 10.1039/d1ob01806j.
4
Visible-Light-Mediated C-I Difluoroallylation with an α-Aminoalkyl Radical as a Mediator.可见光促进的 C-I 二氟烯丙基化反应:α-氨基烷基自由基作为媒介。
Org Lett. 2021 Sep 17;23(18):7306-7310. doi: 10.1021/acs.orglett.1c02905. Epub 2021 Sep 8.
5
A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters.Lewis 碱催化的硼酸盐和酯的光氧化还原活化方法。
Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15136-15140. doi: 10.1002/anie.201709690. Epub 2017 Oct 24.
6
Light-Driven Four-Component Reaction with Boronic Acid Derivatives as Alkylating Agents: An Amine/Imine-Mediated Activation Approach.光驱动的四组分反应:硼酸盐衍生物作为烷基化试剂:一种通过胺/亚胺介导的激活方法。
Org Lett. 2023 Jun 9;25(22):4010-4015. doi: 10.1021/acs.orglett.3c01020. Epub 2023 May 30.
7
Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation.硼活化促进的酮酸的分子间自由基加成。
J Am Chem Soc. 2019 Oct 16;141(41):16237-16242. doi: 10.1021/jacs.9b09099. Epub 2019 Oct 3.
8
Blue Light-Emitting Diode-Induced Direct C-H Functionalization of 1,4-Quinones with Aryl and Alkyl Boronic Acids.蓝光发光二极管诱导的1,4-醌与芳基和烷基硼酸的直接C-H官能化反应
J Org Chem. 2022 Nov 18;87(22):15421-15434. doi: 10.1021/acs.joc.2c01972. Epub 2022 Nov 2.
9
Advances in Rhodium-Catalyzed Oxidative Arene Alkenylation.铑催化氧化芳烃烯基化反应的研究进展
Acc Chem Res. 2020 Apr 21;53(4):920-936. doi: 10.1021/acs.accounts.0c00036. Epub 2020 Apr 2.
10
Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids.钯和可见光介导的未活化卤代烃与芳基硼酸的羰基化铃木-宫浦偶联反应
Chem Commun (Camb). 2017 Jun 22;53(51):6895-6898. doi: 10.1039/c7cc02763j.

引用本文的文献

1
Bromine radical release from a nickel-complex facilitates the activation of alkyl boronic acids: a boron selective Suzuki-Miyaura cross coupling.镍配合物释放溴自由基促进烷基硼酸的活化:一种硼选择性的铃木-宫浦交叉偶联反应。
Chem Sci. 2024 Sep 26;15(42):17490-7. doi: 10.1039/d4sc04196h.
2
Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping.双功能铁催化的炔烃Z-选择性氢烷基化反应以及通过自由基塑造和翻转实现的Z-E串联构型转化
Nat Commun. 2024 Oct 4;15(1):8619. doi: 10.1038/s41467-024-53021-x.
3
The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies.
磺酰肼在电合成中的应用:近期研究综述
ACS Omega. 2022 Oct 27;7(44):39531-39561. doi: 10.1021/acsomega.2c04205. eCollection 2022 Nov 8.
4
The Impact of Boron Hybridisation on Photocatalytic Processes.硼杂化对光催化过程的影响。
Angew Chem Int Ed Engl. 2022 Sep 19;61(38):e202207067. doi: 10.1002/anie.202207067. Epub 2022 Aug 10.
5
Base-Mediated Radical Borylation of Alkyl Sulfones.基于碱的烷基砜的自由基硼化反应。
Chemistry. 2022 Jan 13;28(3):e202103866. doi: 10.1002/chem.202103866. Epub 2021 Nov 29.