• 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

通过钯催化的芳基硼酸与α,β-不饱和酯的串联共轭加成/环化反应合成β,β-二取代茚酮。

Synthesis of β,β-Disubstituted Indanones via the Pd-Catalyzed Tandem Conjugate Addition/Cyclization Reaction of Arylboronic Acids with α,β-Unsaturated Esters.

机构信息

State Key Laboratory of Organometallic Chemistry, ‡Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

出版信息

J Org Chem. 2017 Oct 6;82(19):9988-9994. doi: 10.1021/acs.joc.7b01364. Epub 2017 Sep 13.

DOI:10.1021/acs.joc.7b01364
PMID:28836441
Abstract

Under Pd catalysis with a newly synthesized electron-deficient heterocycle, 2-(4,5-dihydroimidazol-2-yl)pyrimidine (as the ligand), the reaction of α,β-unsaturated esters with arylboronic acids afforded a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. Mechanistic studies revealed that the reaction involves a tandem conjugate addition/1,4-Pd shift followed by a cyclization.

摘要

在新型合成的缺电子杂环(作为配体)的钯催化下,α,β-不饱和酯与芳基硼酸反应生成了一系列含有季碳的 3,3-二取代茚满-1-酮,产率很高。机理研究表明,该反应涉及串联共轭加成/1,4-Pd 迁移,然后是环化。

相似文献

1
Synthesis of β,β-Disubstituted Indanones via the Pd-Catalyzed Tandem Conjugate Addition/Cyclization Reaction of Arylboronic Acids with α,β-Unsaturated Esters.通过钯催化的芳基硼酸与α,β-不饱和酯的串联共轭加成/环化反应合成β,β-二取代茚酮。
J Org Chem. 2017 Oct 6;82(19):9988-9994. doi: 10.1021/acs.joc.7b01364. Epub 2017 Sep 13.
2
Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Carboxylic Acids. Synthesis of β-Quaternary Carbons Substituted Carboxylic Acids.Pd(II)/联吡啶催化的芳基硼酸与α,β-不饱和羧酸的共轭加成反应。β-季碳取代羧酸的合成。
J Org Chem. 2017 Aug 4;82(15):8023-8030. doi: 10.1021/acs.joc.7b01248. Epub 2017 Jul 24.
3
Cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to beta,beta-disubstituted enones: construction of quaternary carbon centers.阳离子 Pd(II)/联吡啶催化的芳基硼酸与β,β-二取代烯酮的共轭加成:季碳原子的构建。
Org Lett. 2010 Jun 4;12(11):2536-9. doi: 10.1021/ol100767u.
4
Divergent Syntheses of Spiroindanones and 2-Substituted 1-Indanones by Ruthenium-Catalyzed Tandem Coupling and Cyclization of Aromatic Acids with α,β-Unsaturated Ketones.通过钌催化的芳酸与α,β-不饱和酮的串联偶联和环化反应,对螺吲哚酮和 2-取代 1-茚酮进行发散合成。
J Org Chem. 2019 Feb 1;84(3):1348-1362. doi: 10.1021/acs.joc.8b02820. Epub 2019 Jan 24.
5
Pd(II)-SDP-catalyzed enantioselective 5-exo-dig cyclization of γ-alkynoic acids: application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center.Pd(II)-SDP 催化的γ-炔基酸的对映选择性 5-exo-内型环化:在手性季碳中心的官能化二氢呋喃-2(3H)-酮合成中的应用。
Org Biomol Chem. 2013 Sep 21;11(35):5936-43. doi: 10.1039/c3ob41103f.
6
Heterogeneous versus homogeneous copper(II) catalysis in enantioselective conjugate-addition reactions of boron in water.水相中硼的对映选择性共轭加成反应中的非均相铜(II)催化与均相铜(II)催化
Chem Asian J. 2014 Jan;9(1):179-88. doi: 10.1002/asia.201300997. Epub 2013 Sep 20.
7
Synthesis of Quaternary-Carbon-Containing β -Amino Acids by the Rh -Catalyzed Enantioselective Arylation of α-Substituted β-Nitroacrylates.通过铑催化的α-取代β-硝基丙烯酸酯的对映选择性芳基化反应合成含季碳的β-氨基酸
Chemistry. 2017 Feb 3;23(8):1830-1838. doi: 10.1002/chem.201604120. Epub 2017 Jan 4.
8
Asymmetric conjugate 1,4-addition of arylboronic acids to alpha, beta-unsaturated esters catalyzed by Rhodium(I)/(S)-binap.铑(I)/(S)-联萘酚催化芳基硼酸与α,β-不饱和酯的不对称共轭1,4-加成反应
J Org Chem. 2000 Sep 22;65(19):5951-5. doi: 10.1021/jo0002184.
9
Pd(II)-bipyridine catalyzed conjugate addition of arylboronic acid to alpha,beta-unsaturated carbonyl compounds.钯(II)-联吡啶催化芳基硼酸与α,β-不饱和羰基化合物的共轭加成反应。
J Org Chem. 2005 Nov 11;70(23):9651-3. doi: 10.1021/jo051561h.
10
Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Lactams: Enantioselective Construction of All-Carbon Quaternary Stereocenters in Saturated Nitrogen-Containing Heterocycles.钯催化芳基硼酸对α,β-不饱和内酰胺的不对称共轭加成:在含氮饱和杂环中对全碳季碳立体中心的对映选择性构建。
Org Lett. 2023 Sep 8;25(35):6479-6484. doi: 10.1021/acs.orglett.3c02064. Epub 2023 Aug 28.

引用本文的文献

1
Unexpected -Heck Reaction under the Catellani Conditions.卡泰拉尼条件下的意外-Heck反应。
Org Lett. 2020 May 15;22(10):3770-3774. doi: 10.1021/acs.orglett.0c00952. Epub 2020 Apr 2.