• 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

高化学选择性和立体选择性的钯催化内炔烃转移顺式氢化反应得到顺式烯烃。

Highly chemo- and stereoselective palladium-catalyzed transfer semihydrogenation of internal alkynes affording cis-alkenes.

机构信息

Department of Chemistry, Tsinghua University, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, China.

出版信息

J Org Chem. 2010 May 7;75(9):2966-70. doi: 10.1021/jo100247a.

DOI:10.1021/jo100247a
PMID:20345142
Abstract

DMF (N,N-dimethylformamide)/KOH was found to be an efficient hydrogen source in the Pd(OAc)(2)-catalyzed transfer semihydrogenation of various functionalized internal alkynes to afford cis-alkenes in good to high yields with excellent chemo- and stereoselectivity. This catalytic process was also applied to the synthesis of analogues of combretastatin A-4.

摘要

DMF(N,N-二甲基甲酰胺)/KOH 被发现是 Pd(OAc)(2)催化的各种官能化内部炔烃转移半氢化反应中有效的氢源,以高产率和优异的化学和立体选择性得到顺式烯烃。该催化过程也被应用于康普瑞汀 A-4 类似物的合成。

相似文献

1
Highly chemo- and stereoselective palladium-catalyzed transfer semihydrogenation of internal alkynes affording cis-alkenes.高化学选择性和立体选择性的钯催化内炔烃转移顺式氢化反应得到顺式烯烃。
J Org Chem. 2010 May 7;75(9):2966-70. doi: 10.1021/jo100247a.
2
Stereodivergent ruthenium-catalyzed transfer semihydrogenation of diaryl alkynes.手性钌催化的二芳基炔烃转移顺式加氢。
Chemistry. 2011 Jul 18;17(30):8462-5. doi: 10.1002/chem.201003662. Epub 2011 Jun 8.
3
Transition-metal-free semihydrogenation of diarylalkynes: highly stereoselective synthesis of trans-alkenes using Na2S·9H2O.无过渡金属参与的二芳基炔烃的半氢化反应:使用 Na2S·9H2O 实现反式烯烃的高立体选择性合成。
Org Lett. 2014 Jun 6;16(11):3020-3. doi: 10.1021/ol501137x. Epub 2014 May 21.
4
Palladium-catalyzed dehydrogenative cis double phosphorylation of alkynes with H-phosphonate leading to (Z)-bisphosphoryl-1-alkenes.钯催化炔烃与亚膦酸酯的脱氢顺式双磷酸化反应生成(Z)-双磷酰基-1-烯烃。
J Am Chem Soc. 2008 Mar 5;130(9):2752-3. doi: 10.1021/ja7108272. Epub 2008 Feb 8.
5
Palladium-catalyzed hydrophenylation of alkynes with sodium tetraphenylborate under mild conditions.钯催化炔烃与四苯基硼酸钠在温和条件下的氢苯基化反应。
J Org Chem. 2008 Jan 18;73(2):558-62. doi: 10.1021/jo7020554. Epub 2007 Dec 14.
6
Selective semihydrogenation of alkynes on shape-controlled palladium nanocrystals.在形貌可控的钯纳米晶上炔烃的选择半氢化。
Chem Asian J. 2013 May;8(5):919-25. doi: 10.1002/asia.201201166. Epub 2013 Mar 6.
7
Palladium-catalyzed difunctionalization of internal alkynes via highly regioselective 6-endo cyclization and alkenylation of enynoates: synthesis of multisubstituted pyrones.钯催化内炔烃通过高度区域选择性的6-内型环化及烯炔酸酯的烯基化实现双官能化:多取代吡喃酮的合成
Org Lett. 2015 Apr 3;17(7):1636-9. doi: 10.1021/acs.orglett.5b00272. Epub 2015 Mar 19.
8
Synthesis of cis-1,2-dihaloalkenes featuring palladium-catalyzed coupling of haloalkynes and α,β-unsaturated carbonyls.钯催化卤代炔烃与α,β-不饱和羰基化合物偶联合成顺式-1,2-二卤代烯烃。
J Org Chem. 2011 May 20;76(10):4071-4. doi: 10.1021/jo102406j. Epub 2011 Apr 19.
9
Synthesis of multiply substituted alkylidene silacyclohexadiene derivatives via palladium-catalyzed insertion of alkynes into alkylidene silacyclobutenes.通过钯催化炔烃插入亚烷基硅环丁烯合成多取代亚烷基硅环己二烯衍生物
J Org Chem. 2007 Apr 13;72(8):3137-40. doi: 10.1021/jo062583m. Epub 2007 Mar 20.
10
Palladium-catalyzed regio- and stereoselective hydrosilylation of electron-deficient alkynes.钯催化的缺电子炔烃的区域和立体选择性硅氢化反应。
Org Lett. 2012 Mar 16;14(6):1552-5. doi: 10.1021/ol300279c. Epub 2012 Feb 23.

引用本文的文献

1
Palladium nanoparticles from β-cyclodextrin and cellulose methyl carboxylate as an effective catalyst for Sonogashira coupling and the reduction of alkynes.以β-环糊精和羧甲基纤维素制备的钯纳米颗粒作为Sonogashira偶联反应及炔烃还原反应的有效催化剂。
RSC Adv. 2025 Apr 4;15(14):10534-10546. doi: 10.1039/d4ra07789j.
2
Structural snapshots of an Al-Cu bond-mediated transformation of terminal acetylenes.铝-铜键介导的末端乙炔转化的结构快照
Chem Sci. 2023 Feb 15;14(11):2866-2876. doi: 10.1039/d3sc00240c. eCollection 2023 Mar 15.
3
Copper-Catalyzed Diboron-Mediated -Semi-Hydrogenation of Alkynes under Facile Conditions.
铜催化二硼试剂介导炔烃在温和条件下的 - 半氢化反应。
Molecules. 2022 Oct 25;27(21):7213. doi: 10.3390/molecules27217213.
4
Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes.泡沫镍上的电化学质子还原用于功能化炔烃的Z-立体选择性半氢化/氘代反应
ChemSusChem. 2022 Jan 10;15(1):e202102221. doi: 10.1002/cssc.202102221. Epub 2021 Dec 16.
5
Amine-Boranes as Transfer Hydrogenation and Hydrogenation Reagents: A Mechanistic Perspective.胺硼烷作为转移氢化和氢化试剂:机理视角
Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14272-14294. doi: 10.1002/anie.202010835. Epub 2021 Feb 25.
6
Catalytic, Transition-Metal-Free Semireduction of Propiolamide Derivatives: Scope and Mechanistic Investigation.催化、过渡金属自由催化丙二酰胺衍生物的半还原:范围和机理研究。
Org Lett. 2020 Sep 4;22(17):7013-7018. doi: 10.1021/acs.orglett.0c02567. Epub 2020 Aug 26.
7
Ligand-Promoted Iridium-Catalyzed Transfer Hydrogenation of Terminal Alkynes with Ethanol and Its Application.配体促进的铱催化末端炔烃与乙醇的转移氢化反应及其应用
ACS Omega. 2019 Sep 18;4(14):16045-16051. doi: 10.1021/acsomega.9b02191. eCollection 2019 Oct 1.
8
Synthesis of (1,3)-1,4-diarylbuta-1,3-dienes promoted by μ-OMs palladium-dimer complex.由μ-OMs钯二聚体配合物促进的(1,3)-1,4-二芳基丁-1,3-二烯的合成。
BMC Chem. 2019 Mar 28;13(1):39. doi: 10.1186/s13065-019-0561-3. eCollection 2019 Dec.
9
Recent Uses of ,-Dimethylformamide and ,-Dimethylacetamide as Reagents.二甲基甲酰胺和二甲基乙酰胺的近期用途。
Molecules. 2018 Aug 3;23(8):1939. doi: 10.3390/molecules23081939.
10
Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors.通过Sonogashira偶联反应合成新型13α-雌酮衍生物作为潜在的17β-羟基类固醇脱氢酶1抑制剂
Beilstein J Org Chem. 2017 Jun 30;13:1303-1309. doi: 10.3762/bjoc.13.126. eCollection 2017.