• 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

在水相介质中合成耐水的铟丙醇盐及其在通过钯催化与酰氯偶联合成 1,4-二羰基化合物中的应用。

Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride.

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

出版信息

J Am Chem Soc. 2010 Nov 17;132(45):15852-5. doi: 10.1021/ja106925f. Epub 2010 Oct 21.

DOI:10.1021/ja106925f
PMID:20964387
Abstract

The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl(3) to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl(2) was used in place of In/InCl(3). The synthetic utility of the indium homoenolate was demonstrated through the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling of indium homoenolate with acid chloride.

摘要

通过铟/三氯化铟(In/InCl3)对烯酮的氧化加成反应,首次合成了耐水性、酮型铟叶立德。该反应仅在水相介质中进行。反应顺利转化需要铟和三氯化铟(InCl3)。当用 InCl 或 InCl2 代替 In/InCl3 时,得到了相似的结果。通过钯催化铟叶立德与酰氯的偶联反应合成 1,4-二羰基化合物,证明了铟叶立德的合成实用性。

相似文献

1
Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride.在水相介质中合成耐水的铟丙醇盐及其在通过钯催化与酰氯偶联合成 1,4-二羰基化合物中的应用。
J Am Chem Soc. 2010 Nov 17;132(45):15852-5. doi: 10.1021/ja106925f. Epub 2010 Oct 21.
2
Direct synthesis of ester-containing indium homoenolate and its application in palladium-catalyzed cross-coupling with aryl halide.直接合成含酯基的铟叶立德及其在钯催化的芳基卤化物交叉偶联反应中的应用。
Chem Commun (Camb). 2011 Apr 28;47(16):4778-80. doi: 10.1039/c0cc05597b. Epub 2011 Mar 17.
3
Multicatalytic synthesis of alpha-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/Friedel-Crafts acylation reaction.通过钯(II)/铟(III)催化的氨氯羰基化/Friedel-Crafts 酰化反应串联催化多相合成α-吡咯烷基酮。
J Am Chem Soc. 2009 Mar 11;131(9):3124-5. doi: 10.1021/ja809897f.
4
Use of InCl(3) as a cocatalyst and a Cl(2)Pd(DPEphos)-P(2-furyl)(3) catalyst system for one-pot hydrometalation-cross-coupling and carbometalation-cross-coupling tandem processes.使用三氯化铟作为助催化剂以及Cl₂Pd(DPEphos)-P(2-呋喃基)₃催化剂体系用于一锅法氢金属化-交叉偶联和碳金属化-交叉偶联串联反应。
Org Lett. 2004 May 13;6(10):1531-4. doi: 10.1021/ol049716f.
5
Palladium-catalyzed cross-coupling of indium homoenolate with aryl halide with wide functional group compatibility.钯催化的吲哚同烯醇盐与芳基卤化物的交叉偶联反应具有广泛的官能团兼容性。
Org Lett. 2011 Feb 4;13(3):422-5. doi: 10.1021/ol102755q. Epub 2010 Dec 23.
6
Mechanistic study of the stereoselective polymerization of D,L-lactide using indium(III) halides.用铟(III)卤化物对 D,L-丙交酯的立体选择性聚合的机理研究。
J Am Chem Soc. 2010 Aug 25;132(33):11649-57. doi: 10.1021/ja103841h.
7
Indium-catalyzed 2-alkenylation of 1,3-dicarbonyl compounds with unactivated alkynes.铟催化的1,3 - 二羰基化合物与未活化炔烃的2 - 烯基化反应
J Am Chem Soc. 2007 Apr 25;129(16):5264-71. doi: 10.1021/ja0702014. Epub 2007 Mar 28.
8
Cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines: synthesis of hyrtinadine A.有机铟金属化合物与2,5-二卤嘧啶的交叉偶联反应:hyrtinadine A的合成
Org Lett. 2008 Sep 4;10(17):3745-8. doi: 10.1021/ol801393n. Epub 2008 Aug 2.
9
Zn/InCl(3)-mediated pinacol cross-coupling reactions of aldehydes with alpha,beta-unsaturated ketones in aqueous media.锌/三氯化铟介导的醛与α,β-不饱和酮在水介质中的频哪醇交叉偶联反应。
Org Lett. 2009 May 21;11(10):2213-5. doi: 10.1021/ol900619d.
10
Synthesis of 3,4-disubstituted maleimides by selective cross-coupling reactions using indium organometallics.使用有机铟试剂通过选择性交叉偶联反应合成3,4-二取代马来酰亚胺。
Org Lett. 2009 Mar 19;11(6):1285-8. doi: 10.1021/ol900063p.

引用本文的文献

1
Mechanisms of Activating Agents to Form Organozinc Reagents from Zinc Metal: Lessons for Reaction Design.从金属锌形成有机锌试剂的活化剂作用机制:反应设计的经验教训
J Org Chem. 2025 Jan 17;90(2):939-948. doi: 10.1021/acs.joc.4c02726. Epub 2025 Jan 2.
2
Visible light induced cooperative carbonylation and (hetero)aryl migration: synthesis of multi-carbonyl compounds.可见光诱导的协同羰基化和(杂)芳基迁移:多羰基化合物的合成
Chem Sci. 2024 Aug 14;15(35):14304-9. doi: 10.1039/d4sc03221g.
3
Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.
未活化烯烃的光催化自由基芳酰化反应:通往β-官能化1,4-、1,6-和1,7-二酮的途径
ACS Catal. 2019 Nov 1;9(11):10358-10364. doi: 10.1021/acscatal.9b03570. Epub 2019 Oct 17.
4
Nickel-catalyzed reductive coupling of homoenolates and their higher homologues with unactivated alkyl bromides.镍催化的偕同烯醇化物及其高同系物与未活化的烷基溴化物的还原偶联反应。
Nat Commun. 2020 Nov 6;11(1):5638. doi: 10.1038/s41467-020-19194-x.
5
Rh(I)/Sc(OTf)-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones.Rh(I)/Sc(OTf)共催化铵叶立德与(E)-1,4-烯二酮的迈克尔加成反应:功能化 1,4-二酮的合成。
Mol Divers. 2019 Nov;23(4):997-1010. doi: 10.1007/s11030-019-09941-8. Epub 2019 Apr 5.
6
A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes.一种通用的脱氧方法,用于从芳香羧酸和烯烃合成酮。
Nat Commun. 2018 Aug 29;9(1):3517. doi: 10.1038/s41467-018-06019-1.
7
Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones.通过烯醇鎓物种实现不同酮烯醇盐的交叉偶联,以得到非对称的1,4 - 二酮。
Beilstein J Org Chem. 2018 May 3;14:992-997. doi: 10.3762/bjoc.14.84. eCollection 2018.
8
α-Silyl Amides: Effective Bifunctional Lynchpins for Type I Anion Relay Chemistry.α-硅基酰胺:I 型阴离子接力化学的有效双功能连接基。
Org Lett. 2017 Nov 17;19(22):6216-6219. doi: 10.1021/acs.orglett.7b03142. Epub 2017 Nov 9.