• 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

芳基三氟甲磺酸酯与亚磷酸三烷基酯的光诱导无过渡金属和外部光敏剂的交叉偶联反应。

Photoinduced transition-metal and external photosensitizer free cross-coupling of aryl triflates with trialkyl phosphites.

作者信息

Dou Qian, Geng Li, Cheng Bin, Li Chao-Jun, Zeng Huiying

机构信息

Institute of Marine Biomedicine, Shenzhen Polytechnic, Shenzhen 518055, China.

出版信息

Chem Commun (Camb). 2021 Sep 4;57(68):8429-8432. doi: 10.1039/d1cc03496k. Epub 2021 Aug 4.

DOI:10.1039/d1cc03496k
PMID:34346433
Abstract

Photoinduced phosphonation of aryl triflates with trialkyl phosphites via a tandem single-electron-transfer, C-O bond cleavage and Arbuzov rearrangement process in the absence of transition-metal and external photosensitizer is reported herein. The protocol features good functional group compatibility and mild reaction conditions, providing various aryl phosphates in good to high yields. Furthermore, this strategy allows the late-stage phosphonation of complex and biologically active compounds.

摘要

本文报道了在无过渡金属和外部光敏剂的情况下,芳基三氟甲磺酸酯与亚磷酸三烷基酯通过串联单电子转移、C-O键裂解和阿尔布佐夫重排过程进行的光诱导膦酰化反应。该方法具有良好的官能团兼容性和温和的反应条件,能以良好至高收率提供各种芳基磷酸酯。此外,该策略还允许对复杂的生物活性化合物进行后期膦酰化。

相似文献

1
Photoinduced transition-metal and external photosensitizer free cross-coupling of aryl triflates with trialkyl phosphites.芳基三氟甲磺酸酯与亚磷酸三烷基酯的光诱导无过渡金属和外部光敏剂的交叉偶联反应。
Chem Commun (Camb). 2021 Sep 4;57(68):8429-8432. doi: 10.1039/d1cc03496k. Epub 2021 Aug 4.
2
Photoinduced transition-metal- and external-photosensitizer-free intramolecular aryl rearrangement C(Ar)-O bond cleavage.光诱导的无过渡金属和外部光敏剂的分子内芳基重排C(Ar)-O键裂解。
Chem Sci. 2020 May 26;11(22):5740-5744. doi: 10.1039/d0sc01585g. eCollection 2020 Jun 14.
3
Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C-O bond cleavage.通过选择性C-O键裂解实现芳基三氟甲磺酸酯的有机介导电化学氟磺酰化反应。
Nat Commun. 2023 Oct 31;14(1):6933. doi: 10.1038/s41467-023-42699-0.
4
Transition-metal-free cross-coupling of thioethers with aryl(cyano)iodonium triflates: a facile and efficient method for the one-pot synthesis of thiocyanates.硫醚与芳基(氰基)三氟甲磺酸碘鎓盐的无过渡金属交叉偶联:一种简便高效的一锅法合成硫氰酸盐的方法。
Chem Commun (Camb). 2015 Apr 28;51(33):7180-3. doi: 10.1039/c5cc00875a.
5
Transition-Metal-Free Anti-Markovnikov Hydroarylation of Alkenes with Aryl Chlorides through Consecutive Photoinduced Electron Transfer.通过连续光诱导电子转移实现的烯烃与芳基氯的无过渡金属反马氏氢芳基化反应
Org Lett. 2024 Feb 16;26(6):1265-1270. doi: 10.1021/acs.orglett.4c00106. Epub 2024 Feb 6.
6
Regioselective O/C phosphorylation of α-chloroketones: a general method for the synthesis of enol phosphates and β-ketophosphonates Perkow/Arbuzov reaction.α-氯代酮的区域选择性氧/碳磷酸化:烯醇磷酸酯和β-酮基膦酸酯合成的通用方法 佩尔科夫/阿尔布佐夫反应。
RSC Adv. 2020 Aug 11;10(49):29493-29497. doi: 10.1039/d0ra05140c. eCollection 2020 Aug 5.
7
Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature.芳基三氟甲磺酸酯简单高效地生成芳基自由基:室温下芳基硼酸酯和芳基碘化物的合成。
J Am Chem Soc. 2017 Jun 28;139(25):8621-8627. doi: 10.1021/jacs.7b03538. Epub 2017 Jun 20.
8
Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation.芳基碘化物的无金属光诱导硫化及其他硫属化反应
Front Chem. 2022 Jul 26;10:941016. doi: 10.3389/fchem.2022.941016. eCollection 2022.
9
Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage.镍催化芳基三氟甲磺酸酯与硫代碳酸酯通过C-O/C-O键断裂的交叉亲电偶联反应
Org Lett. 2021 Mar 19;23(6):2158-2163. doi: 10.1021/acs.orglett.1c00313. Epub 2021 Mar 1.
10
Cleavage of the Robust Silicon-Fluorine σ-Bond Allows Silicon-Carbon Bond Formation: Synthetic Strategies Toward Ortho-Silyl Aryl Phosphonates.稳定的硅-氟σ键的裂解促进硅-碳键的形成:邻硅基芳基膦酸酯的合成策略
Angew Chem Int Ed Engl. 2025 Jan 15;64(3):e202413759. doi: 10.1002/anie.202413759. Epub 2024 Nov 2.

引用本文的文献

1
Intermolecular C-C/C-N σ-bond metathesis enabled by visible light.可见光驱动的分子间碳-碳/碳-氮σ键复分解反应
Chem Sci. 2024 Jul 12;15(32):12900-12905. doi: 10.1039/d4sc02412e. eCollection 2024 Aug 14.
2
Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C-O bond cleavage.通过选择性C-O键裂解实现芳基三氟甲磺酸酯的有机介导电化学氟磺酰化反应。
Nat Commun. 2023 Oct 31;14(1):6933. doi: 10.1038/s41467-023-42699-0.
3
Site-selective and metal-free C-H phosphonation of arenes photoactivation of thianthrenium salts.
芳烃的位点选择性无金属C-H膦酰化反应:噻蒽盐的光活化
RSC Adv. 2023 Aug 8;13(33):23359-23364. doi: 10.1039/d3ra04512a. eCollection 2023 Jul 26.
4
Visible-light-induced cross-coupling of aryl iodides with hydrazones an EDA-complex.可见光诱导的芳基碘化物与腙的交叉偶联——一种电子给体-受体复合物。
Chem Sci. 2022 May 23;13(24):7165-7171. doi: 10.1039/d2sc01909d. eCollection 2022 Jun 22.
5
C-P bond formation of cyclophanyl-, and aryl halides a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds.环芳基卤化物和芳基卤化物的C-P键形成:紫外光诱导的光Arbuzov反应——通往膦酸酯接枝支架的通用途径
RSC Adv. 2022 Jan 25;12(6):3309-3312. doi: 10.1039/d2ra00094f. eCollection 2022 Jan 24.
6
Visible-light-induced transition metal and photosensitizer free decarbonylative addition of amino-arylaldehydes to ketones.可见光诱导的无过渡金属和光敏剂的氨基芳基醛与酮的脱羰加成反应。
Chem Sci. 2021 Dec 21;13(3):698-703. doi: 10.1039/d1sc06278f. eCollection 2022 Jan 19.