• 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

用于合成()-乙烯基膦酸酯的炔烃的选择性氢膦酰化反应

Selective hydrophosphorylation of alkynes for the synthesis of ()-vinylphosphonates.

作者信息

Kaboudin Babak, Esfandiari Hesam, Arshadi Nematollah, Fukaya Haruhiko

机构信息

Department of Chemistry, Institute for Advanced Studies in Basic Sciences Gava Zang Zanjan Iran

Department of Chemistry, Faculty of Sciences, University of Zanjan Zanjan Iran.

出版信息

RSC Adv. 2025 Feb 17;15(7):5338-5343. doi: 10.1039/d5ra00300h. eCollection 2025 Feb 13.

DOI:10.1039/d5ra00300h
PMID:39963455
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11831965/
Abstract

Hydrophosphorylation of alkynes with dialkylphosphites in the various copper catalysts was investigated. The reactions provided the regio- and stereoselective -vinylphosphonates under commercially available copper chloride catalyst in the presence of ethylene diamine as an efficient ligand. The impact of solvents, temperature, and diamine ligands are included in this report. In addition, the DFT calculations provided insight into the regio- and stereoselectivity of the reaction. It is suggested that the reaction proceeded an generated Cu(AN) complex. The reaction of phenylacetylene with diethyl phosphite in the presence of EDA and the (CHCN)CuBF complex as a catalyst also gave the corresponding -vinylphosphonates in good yield.

摘要

研究了在各种铜催化剂存在下,炔烃与亚磷酸二烷基酯的氢磷酸化反应。在市售氯化铜催化剂存在下,以乙二胺作为有效配体,这些反应提供了区域和立体选择性的β-乙烯基膦酸酯。本报告包括了溶剂、温度和二胺配体的影响。此外,密度泛函理论(DFT)计算为该反应的区域和立体选择性提供了深入了解。有人认为该反应通过生成Cu(AN)络合物进行。在EDA和(CHCN)CuBF络合物作为催化剂存在下,苯乙炔与亚磷酸二乙酯的反应也以良好的产率得到了相应的β-乙烯基膦酸酯。

相似文献

1
Selective hydrophosphorylation of alkynes for the synthesis of ()-vinylphosphonates.用于合成()-乙烯基膦酸酯的炔烃的选择性氢膦酰化反应
RSC Adv. 2025 Feb 17;15(7):5338-5343. doi: 10.1039/d5ra00300h. eCollection 2025 Feb 13.
2
Copper-catalyzed stereo- and regioselective hydrophosphorylation of terminal alkynes: scope and mechanistic study.铜催化末端炔烃的立体和区域选择性氢膦酰化反应:范围及机理研究
RSC Adv. 2022 Jun 29;12(29):18889-18896. doi: 10.1039/d2ra02908a. eCollection 2022 Jun 22.
3
Ligand-Dependent-Controlled Copper-Catalyzed Regio- and Stereoselective Silaboration of Alkynes.配体依赖性控制的铜催化炔烃的区域和立体选择性硅硼化反应
Org Lett. 2019 Aug 2;21(15):6016-6020. doi: 10.1021/acs.orglett.9b02160. Epub 2019 Jul 18.
4
Copper-Catalysed Synthesis of (E)-Allylic Organophosphorus Derivatives: A Low Toxic, Mild, Economical, and Ligand-Free Method.铜催化合成(E)-烯丙基有机磷衍生物:一种低毒、温和、经济且无配体的方法。
ChemSusChem. 2025 Jan 14;18(2):e202401450. doi: 10.1002/cssc.202401450. Epub 2024 Oct 25.
5
ZnCl-mediated stereo- and chemoselective synthesis of vinylphosphonates.ZnCl 介导的乙烯基膦酸酯的立体和化学选择性合成。
Org Biomol Chem. 2022 Mar 23;20(12):2500-2507. doi: 10.1039/d2ob00037g.
6
Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.对映选择性和非对映选择性铜催化炔烃与烯丙基 gem-二氯代物的加成反应。
Angew Chem Int Ed Engl. 2022 Jun 7;61(23):e202117696. doi: 10.1002/anie.202117696. Epub 2022 Mar 21.
7
Regio- and Stereoselective Hydroalkynylation of Internal Alkynes with Terminal Alkynes by Half-Sandwich Rare-Earth Catalysts.半夹心稀土催化剂催化内炔与端炔的区域和立体选择性氢炔基化反应
J Am Chem Soc. 2025 Feb 19;147(7):6149-6161. doi: 10.1021/jacs.4c17210. Epub 2025 Feb 5.
8
Copper-Catalyzed Enantioselective Hydrophosphorylation of Unactivated Alkynes.铜催化未活化炔烃的对映选择性氢膦酰化反应
Angew Chem Int Ed Engl. 2025 Jan 15;64(3):e202415314. doi: 10.1002/anie.202415314. Epub 2024 Nov 6.
9
Computational Study Revealing the Mechanistic Origin of Distinct Performances of P(O)-H/OH Compounds in Palladium-Catalyzed Hydrophosphorylation of Terminal Alkynes: Switchable Mechanisms and Potential Side Reactions.计算研究揭示了 P(O)-H/OH 化合物在钯催化末端炔烃的氢膦酰化反应中表现出不同性能的机制起源:可切换的机制和潜在的副反应。
J Org Chem. 2022 Nov 4;87(21):14673-14684. doi: 10.1021/acs.joc.2c02002. Epub 2022 Oct 13.
10
Copper-Catalyzed Regio- and Stereoselective Hydrothiolation of Allenamides, Enamides, and Ynamides.铜催化的烯丙酰胺、烯酰胺和炔酰胺的区域和立体选择性氢硫基化反应
J Org Chem. 2023 Jan 20;88(2):1168-1176. doi: 10.1021/acs.joc.2c02716. Epub 2023 Jan 4.

本文引用的文献

1
Stereoselective synthesis of vinylphosphonates through aromatic aza-Claisen rearrangement of α-aminophosphonates.通过 α-氨基膦酸酯的芳基氮杂-Claisen 重排反应立体选择性合成乙烯基膦酸酯。
Chem Commun (Camb). 2023 Jun 6;59(46):7076-7079. doi: 10.1039/d3cc01669b.
2
Copper-catalyzed stereo- and regioselective hydrophosphorylation of terminal alkynes: scope and mechanistic study.铜催化末端炔烃的立体和区域选择性氢膦酰化反应:范围及机理研究
RSC Adv. 2022 Jun 29;12(29):18889-18896. doi: 10.1039/d2ra02908a. eCollection 2022 Jun 22.
3
ZnCl-mediated stereo- and chemoselective synthesis of vinylphosphonates.
ZnCl 介导的乙烯基膦酸酯的立体和化学选择性合成。
Org Biomol Chem. 2022 Mar 23;20(12):2500-2507. doi: 10.1039/d2ob00037g.
4
Cobalt Catalyzed C-P Bond Formation by Cross-Coupling of Boronic Acids with P(O)H Compounds in Presence of Zinc.钴催化硼酸与 P(O)H 化合物在锌存在下的交叉偶联形成 C-P 键。
Molecules. 2020 Jan 10;25(2):290. doi: 10.3390/molecules25020290.
5
Cu-Catalyzed Direct C-P Bond Formation through Dehydrogenative Cross-Coupling Reactions between Azoles and Dialkyl Phosphites.铜催化唑类化合物与亚磷酸二烷基酯之间的脱氢交叉偶联反应直接形成碳-磷键
J Org Chem. 2019 Jun 7;84(11):6868-6878. doi: 10.1021/acs.joc.9b00670. Epub 2019 May 30.
6
Hydrophosphorylation of Alkynes Catalyzed by Palladium: Generality and Mechanism.炔烃的钯催化水膦化:普遍性和机理。
J Am Chem Soc. 2018 Feb 28;140(8):3139-3155. doi: 10.1021/jacs.8b00550. Epub 2018 Feb 19.
7
Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates.碱介导的α-取代乙烯基膦酸酯与重氮化合物的1,3-偶极环加成反应合成3-吡唑基膦酸酯和5-吡唑羧酸酯。
Org Biomol Chem. 2016 Oct 25;14(42):10000-10010. doi: 10.1039/c6ob01780k.
8
Design, synthesis, anticancer, antimicrobial activities and molecular docking studies of theophylline containing acetylenes and theophylline containing 1,2,3-triazoles with variant nucleoside derivatives.含乙炔基的茶碱及含1,2,3-三唑并带有可变核苷衍生物的茶碱的设计、合成、抗癌、抗菌活性及分子对接研究
Eur J Med Chem. 2016 Nov 10;123:379-396. doi: 10.1016/j.ejmech.2016.07.024. Epub 2016 Jul 15.
9
Intramolecular heterocyclization of O-propargylated aromatic hydroxyaldehydes as an expedient route to substituted chromenopyridines under metal-free conditions.在无金属条件下,O-炔丙基化芳香族羟基醛的分子内杂环化反应是合成取代色烯并吡啶的便捷途径。
Org Lett. 2015 Feb 20;17(4):964-7. doi: 10.1021/acs.orglett.5b00067. Epub 2015 Feb 5.
10
C-P bond-forming reactions via C-O/P-H cross-coupling catalyzed by nickel.镍催化的 C-O/P-H 交叉偶联 C-P 键形成反应。
J Am Chem Soc. 2015 Feb 11;137(5):1782-5. doi: 10.1021/ja512498u. Epub 2015 Jan 30.