• 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

三溴化铟催化烯醇醚与甲硅烷基烯酮亚胺的偶联反应合成β,γ-不饱和腈

Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward the Synthesis of β,γ-Unsaturated Nitriles.

作者信息

Nishimoto Yoshihiro, Nishimura Takashi, Yasuda Makoto

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan).

Frontier Research Base for Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan).

出版信息

Chemistry. 2015 Dec 7;21(50):18301-8. doi: 10.1002/chem.201503414. Epub 2015 Oct 30.

DOI:10.1002/chem.201503414
PMID:26515612
Abstract

Herein, a coupling reaction of enol ethers with silyl ketene imines in the presence of catalytic amounts of InBr3 and Me3 SiBr is described. Kinetic studies have revealed that an indium catalyst and Me3 SiBr accelerated the coupling process and the regeneration of the catalyst, respectively. Various types of enol ethers and silyl ketene imines are applicable. In addition, a formal synthesis of verapamil was achieved by using this novel coupling reaction.

摘要

在此,描述了在催化量的三溴化铟和三甲基硅溴存在下烯醇醚与甲硅烷基烯酮亚胺的偶联反应。动力学研究表明,铟催化剂和三甲基硅溴分别加速了偶联过程和催化剂的再生。各种类型的烯醇醚和甲硅烷基烯酮亚胺均适用。此外,通过使用这种新型偶联反应实现了维拉帕米的形式合成。

相似文献

1
Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward the Synthesis of β,γ-Unsaturated Nitriles.三溴化铟催化烯醇醚与甲硅烷基烯酮亚胺的偶联反应合成β,γ-不饱和腈
Chemistry. 2015 Dec 7;21(50):18301-8. doi: 10.1002/chem.201503414. Epub 2015 Oct 30.
2
Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides.三卤化镓催化的烯醇衍生物与甲硅烷基乙烯酮缩醛的偶联反应
Chemistry. 2016 Aug 8;22(33):11837-45. doi: 10.1002/chem.201602150. Epub 2016 Jul 11.
3
Rhenium-Catalyzed Decarboxylative Coupling of Cyclic Enol Carbonates with Silyl Enol Ethers and Ketene Silyl Acetals.铼催化环状烯醇碳酸酯与烯醇硅醚及烯酮硅基缩醛的脱羧偶联反应
Org Lett. 2023 Apr 7;25(13):2275-2279. doi: 10.1021/acs.orglett.3c00543. Epub 2023 Mar 23.
4
Catalytic asymmetric protonation of silyl ketene imines.硅烯酮亚胺的催化不对称质子化反应。
J Am Chem Soc. 2013 Feb 13;135(6):2100-3. doi: 10.1021/ja312141b. Epub 2013 Jan 30.
5
InCl3/Me3SiBr-catalyzed direct coupling between silyl ethers and enol acetates.InCl3/Me3SiBr 催化的硅醚与烯醇乙酸酯的直接偶联反应。
Org Lett. 2011 May 20;13(10):2762-5. doi: 10.1021/ol200875m. Epub 2011 Apr 28.
6
W(CO)5(L)-catalyzed endo-selective cyclization of allenyl silyl enol ethers: an efficient method for the cyclopentene annulation onto alpha,beta-unsaturated ketones.W(CO)₅(L)催化的烯丙基硅基烯醇醚的内型选择性环化反应:一种将环戊烯环化到α,β-不饱和酮上的有效方法。
Org Lett. 2003 May 15;5(10):1725-8. doi: 10.1021/ol034365a.
7
Mild and efficient pentafluorophenylammonium triflate (PFPAT)-catalyzed C-acylations of enol silyl ethers or ketene silyl (Thio)acetals with acid chlorides.温和且高效的五氟苯基三氟甲磺酸铵(PFPAT)催化烯醇硅醚或烯酮硅(硫)缩醛与酰氯的C-酰化反应。
Org Lett. 2007 May 10;9(10):1859-62. doi: 10.1021/ol070191b. Epub 2007 Apr 13.
8
Asymmetric synthesis of β-amino nitriles through a Sc(III)-catalyzed three-component Mannich reaction of silyl ketene imines.通过硅基烯酮亚胺的钪(III)催化三组分曼尼希反应不对称合成β-氨基腈。
Angew Chem Int Ed Engl. 2013 Mar 18;52(12):3473-7. doi: 10.1002/anie.201209093. Epub 2013 Feb 13.
9
Regio- and Stereoselective Carboindation of Internal Alkynyl Ethers with Organosilicon or -stannane Nucleophiles.内炔基醚与有机硅或有机锡亲核试剂的区域和立体选择性碳环化反应
J Org Chem. 2019 Nov 1;84(21):13345-13363. doi: 10.1021/acs.joc.9b01505. Epub 2019 Sep 9.
10
Synthesis of (Z)-β-(Carbonylamino)alkenylindium through Regioselective anti-Carboindation of Ynamides and Its Transformation to Multisubstituted Enamides.通过炔酰胺的区域选择性反碳金属化反应合成(Z)-β-(羰基氨基)烯基二价铟及其转化为多取代烯酰胺。
Chemistry. 2020 Apr 16;26(22):4930-4934. doi: 10.1002/chem.201905175. Epub 2020 Feb 21.

引用本文的文献

1
Carbometalation and Heterometalation of Carbon-Carbon Multiple-Bonds Using Group-13 Heavy Metals: Carbogallation, Carboindation, Heterogallation, and Heteroindation.使用第13族重金属对碳-碳多重键进行碳金属化和杂金属化:碳镓化、碳铟化、杂镓化和杂铟化。
Chem Asian J. 2020 Mar 16;15(6):636-650. doi: 10.1002/asia.201901730. Epub 2020 Feb 18.