• 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

多组分反应:Pd/Cu 催化酰氯和炔烃的偶联和硼化反应生成 β-硼基酮。

Multicomponent Reaction: Pd/Cu-Catalyzed Coupling and Boration of Acyl Chlorides and Alkynes to β-Boryl Ketones.

机构信息

School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China.

出版信息

J Org Chem. 2023 Apr 7;88(7):4352-4358. doi: 10.1021/acs.joc.2c02953. Epub 2023 Mar 17.

DOI:10.1021/acs.joc.2c02953
PMID:36929949
Abstract

An unprecedented and challenging multicomponent reaction has been developed that allows for the direct transformation of acyl chlorides with alkynes into the corresponding saturated β-boryl ketones via Pd/Cu-catalyzed coupling and boration with ethyl acetate as the hydrogen sources. Various β-boryl ketones were synthesized in good to excellent yields with broad functional group tolerance. In addition, the introduction of boron groups into the products provides substantial opportunities for further conversions.

摘要

发展了一种前所未有的多组分反应,通过 Pd/Cu 催化偶联和以乙酸乙酯为氢源的硼化作用,可将酰氯与炔烃直接转化为相应的饱和β-硼酸酮。各种β-硼酸酮以良好至优异的产率合成,具有广泛的官能团容忍度。此外,产物中硼基团的引入为进一步转化提供了大量机会。

相似文献

1
Multicomponent Reaction: Pd/Cu-Catalyzed Coupling and Boration of Acyl Chlorides and Alkynes to β-Boryl Ketones.多组分反应:Pd/Cu 催化酰氯和炔烃的偶联和硼化反应生成 β-硼基酮。
J Org Chem. 2023 Apr 7;88(7):4352-4358. doi: 10.1021/acs.joc.2c02953. Epub 2023 Mar 17.
2
Multicomponent Reaction: Pd/Cu-Catalyzed Borocarbonylation of Aryldiazonium Salts with Aliphatic Terminal Alkynes to gem-Bis(boryl) Ketones.多组分反应:钯/铜催化芳基重氮盐与脂肪族端炔的硼羰基化反应合成偕二(硼基)酮
Chemistry. 2023 Sep 26;29(54):e202301826. doi: 10.1002/chem.202301826. Epub 2023 Aug 24.
3
Regioselective catalytic carbonylation and borylation of alkynes with aryldiazonium salts toward α-unsubstituted β-boryl ketones.芳基重氮盐与炔烃的区域选择性催化羰基化和硼化反应制备α-未取代的β-硼基酮
Chem Sci. 2022 Sep 30;13(41):12122-12126. doi: 10.1039/d2sc04867a. eCollection 2022 Oct 26.
4
Four-Component Borocarbonylation of Vinylarenes Enabled by Cooperative Cu/Pd Catalysis: Access to β-Boryl Ketones and β-Boryl Vinyl Esters.铜/钯协同催化实现的乙烯基芳烃的四组分硼羰基化反应:合成β-硼基酮和β-硼基乙烯基酯
Angew Chem Int Ed Engl. 2020 Sep 21;59(39):17055-17061. doi: 10.1002/anie.202006427. Epub 2020 Aug 7.
5
Synthesis of α-Boryl Ketones via Hydration or Oxidation of B(MIDA)-Decorated Alkynes.通过 B(MIDA)-修饰的炔烃的水合或氧化反应合成 α-硼基酮。
Org Lett. 2023 Feb 24;25(7):1099-1103. doi: 10.1021/acs.orglett.2c04343. Epub 2023 Feb 15.
6
Copper-Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β-Boryl Ketones.铜催化未活化烯烃与卤代烃的区域选择性硼羰基化偶联反应:β-硼基酮的合成
Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10451-10455. doi: 10.1002/anie.202002714. Epub 2020 Apr 28.
7
Copper-Catalyzed Transformations Using Cu-H, Cu-B, and Cu-Si as Active Catalyst Species.铜催化转化:使用 Cu-H、Cu-B 和 Cu-Si 作为活性催化剂物种。
Chem Rec. 2016 Oct;16(5):2294-2313. doi: 10.1002/tcr.201600039. Epub 2016 Jul 6.
8
Cu(I)-catalyzed cross-coupling of conjugated ene-yne-ketones and terminal alkynes: synthesis of furan-substituted allenes.铜(I)催化的共轭烯炔酮与末端炔烃的交叉偶联:呋喃取代的丙二烯的合成。
Org Lett. 2014 Aug 15;16(16):4082-5. doi: 10.1021/ol501747f. Epub 2014 Jul 30.
9
Structure and reactivity of a preactivated sp2-sp3 diboron reagent: catalytic regioselective boration of α,β-unsaturated conjugated compounds.预活化的 sp2-sp3 二硼试剂的结构和反应性:α,β-不饱和共轭化合物的催化区域选择性硼化反应。
J Org Chem. 2011 May 20;76(10):3997-4007. doi: 10.1021/jo2003488. Epub 2011 Apr 28.
10
Cross-coupling reaction of alkyl halides with grignard reagents catalyzed by Ni, Pd, or Cu complexes with pi-carbon ligand(s).由镍、钯或铜与π-碳配体形成的配合物催化的卤代烃与格氏试剂的交叉偶联反应。
Acc Chem Res. 2008 Nov 18;41(11):1545-54. doi: 10.1021/ar800138a.

引用本文的文献

1
Approach Toward Stereoselective α-Arylation by Pd/Cu-Catalyzed Arylboration of Electron Deficient Alkenes.通过钯/铜催化缺电子烯烃的芳基硼化实现立体选择性α-芳基化的方法
Angew Chem Int Ed Engl. 2025 May 26;64(22):e202424073. doi: 10.1002/anie.202424073. Epub 2025 Mar 27.
2
Synthesis of a bistriazolyl-phenanthroline-Cu(ii) complex immobilized on nanomagnetic iron oxide as a novel green catalyst for synthesis of imidazoles annulation reactions.一种固定在纳米磁性氧化铁上的双三唑基-菲咯啉-Cu(II)配合物的合成,作为用于咪唑环化反应合成的新型绿色催化剂。
Nanoscale Adv. 2023 Sep 29;5(22):6177-6193. doi: 10.1039/d3na00653k. eCollection 2023 Nov 7.