• 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

镍/NN 钳形配体配合物催化的烷基锌试剂与溴化苄的羰基偶联反应。

Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN  Pincer Ligand Complex.

机构信息

Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus C, Denmark.

出版信息

Angew Chem Int Ed Engl. 2018 Jan 15;57(3):800-804. doi: 10.1002/anie.201710089. Epub 2017 Dec 18.

DOI:10.1002/anie.201710089
PMID:29193522
Abstract

An efficient catalytic protocol for the three-component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel-catalyzed carbonylative coupling of two sp -carbon fragments. The method, which relies on the application of nickel complexed with an NN -type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon-centered radicals.

摘要

描述了一种高效的催化三组分反应体系,可将苄基溴化物、一氧化碳和烷基锌试剂组装成苄基烷基酮,这代表了首例镍催化的两个 sp 碳片段的羰基偶联反应。该方法依赖于镍配合 NN 型钳形配体和从固体前体制备中释放 CO 气体的控制,适用于一系列苄基溴化物。机理研究表明其涉及到碳中心自由基的中间产物。

相似文献

1
Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN  Pincer Ligand Complex.镍/NN 钳形配体配合物催化的烷基锌试剂与溴化苄的羰基偶联反应。
Angew Chem Int Ed Engl. 2018 Jan 15;57(3):800-804. doi: 10.1002/anie.201710089. Epub 2017 Dec 18.
2
Direct Access to Isotopically Labeled Aliphatic Ketones Mediated by Nickel(I) Activation.镍(I)活化介导的对映选择性手性酮的直接转化。
Angew Chem Int Ed Engl. 2020 May 18;59(21):8099-8103. doi: 10.1002/anie.201916391. Epub 2020 Mar 2.
3
Nickel-Catalyzed Carbonylative Negishi Cross-Coupling of Unactivated Secondary Alkyl Electrophiles with 1 atm CO Gas.镍催化未活化仲烷基亲电试剂与1个大气压一氧化碳气体的羰基化根岸交叉偶联反应
J Am Chem Soc. 2024 Mar 27;146(12):7971-7978. doi: 10.1021/jacs.4c02023. Epub 2024 Mar 14.
4
Picolinamide Ligands: Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Bromocyclopropane and Beyond.吡啶甲酰胺配体:镍催化芳基溴化物与溴环丙烷及其他化合物的还原交叉偶联反应
Chem Asian J. 2023 Jan 17;18(2):e202201132. doi: 10.1002/asia.202201132. Epub 2022 Dec 15.
5
Nickel-catalyzed allylic carbonylative coupling of alkyl zinc reagents with tert-butyl isocyanide.镍催化的烷基锌试剂与叔丁基异腈的烯丙基羰基化偶联反应。
Nat Commun. 2020 Jan 20;11(1):392. doi: 10.1038/s41467-020-14320-1.
6
Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents.通过镍催化α-溴腈与烷基锌试剂的羰基化偶联反应制备β-酮腈
Chemistry. 2019 Jul 25;25(42):9856-9860. doi: 10.1002/chem.201902206. Epub 2019 Jul 1.
7
Synthesis of Aliphatic Carboxamides Mediated by Nickel NN -Pincer Complexes and Adaptation to Carbon-Isotope Labeling.镍 NN-钳形配合物介导的脂肪族羧酰胺的合成及对碳同位素标记的适应性。
Chemistry. 2018 Oct 9;24(56):14946-14949. doi: 10.1002/chem.201804077. Epub 2018 Sep 11.
8
Methods and Mechanisms for Cross-Electrophile Coupling of Csp(2) Halides with Alkyl Electrophiles.Csp(2)卤化物与烷基亲电试剂交叉亲电偶联的方法和机制
Acc Chem Res. 2015 Jun 16;48(6):1767-75. doi: 10.1021/acs.accounts.5b00057. Epub 2015 May 26.
9
Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates.镍催化苄基锌试剂与芳基溴化物、氯化物和甲苯磺酸盐的交叉偶联反应。
Chem Commun (Camb). 2008 Jul 14(26):3046-8. doi: 10.1039/b803072c. Epub 2008 Apr 24.
10
Cobalt-catalyzed cross-coupling reactions of alkyl halides with allylic and benzylic Grignard reagents and their application to tandem radical cyclization/cross-coupling reactions.钴催化卤代烃与烯丙基和苄基格氏试剂的交叉偶联反应及其在串联自由基环化/交叉偶联反应中的应用。
Chemistry. 2004 Nov 5;10(22):5640-8. doi: 10.1002/chem.200400545.

引用本文的文献

1
Electrochemical Synergistic Ni/Co-Catalyzed Carbonylative Cross-Electrophile Coupling of Aryl and Alkyl Halides with CO.电化学协同镍/钴催化芳基卤化物和烷基卤化物与一氧化碳的羰基化交叉亲电偶联反应
JACS Au. 2025 Mar 5;5(3):1413-1420. doi: 10.1021/jacsau.5c00031. eCollection 2025 Mar 24.
2
Nickel-catalyzed acylzincation of allenes with organozincs and CO.镍催化的丙二烯与有机锌试剂及一氧化碳的酰基锌化反应
Nat Commun. 2023 Oct 31;14(1):6960. doi: 10.1038/s41467-023-42716-2.
3
Palladium-Catalyzed Carbonylative Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates.
由不稳定烯醇盐引发的钯催化未活化烯烃的羰基双官能化反应
Angew Chem Int Ed Engl. 2023 Sep 25;62(39):e202307455. doi: 10.1002/anie.202307455. Epub 2023 Aug 21.
4
Late-Stage Carbon-14 Labeling and Isotope Exchange: Emerging Opportunities and Future Challenges.晚期碳-14标记与同位素交换:新机遇与未来挑战
JACS Au. 2022 Jun 7;2(6):1234-1251. doi: 10.1021/jacsau.2c00030. eCollection 2022 Jun 27.
5
Ruthenium pincer complex-catalyzed heterocycle compatible alkoxycarbonylation of alkyl iodides: substrate keeps the catalyst active.钌钳形配合物催化的烷基碘的杂环兼容烷氧基羰基化反应:底物使催化剂保持活性。
Chem Sci. 2022 Feb 7;13(8):2481-2486. doi: 10.1039/d1sc06581e. eCollection 2022 Feb 23.
6
Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN pincer ligand.镍催化的去氨基 Sonogashira 偶联反应,通过 NN 钳形配体实现了烷基吡啶𬭩盐的反应。
Nat Commun. 2021 Aug 12;12(1):4904. doi: 10.1038/s41467-021-25222-1.