• 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

通过钯催化的双重 C-H 键活化和烯醇环化反应,从仲烷基芳基酮和芳基卤化物合成菲并[9,10-d]恶嗪衍生物。

Synthesis of phenanthrone derivatives from sec-alkyl aryl ketones and aryl halides via a palladium-catalyzed dual C-H bond activation and enolate cyclization.

机构信息

Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.

出版信息

J Am Chem Soc. 2010 Jun 30;132(25):8569-71. doi: 10.1021/ja1026248.

DOI:10.1021/ja1026248
PMID:20524609
Abstract

A palladium-catalyzed chelation-assisted C-H activation of alkyl aryl ketones and their reaction with aryl iodides to afford ortho-arylated products is described. For sec-alkyl aryl ketones, the catalytic reaction proceeds further to give 10,10-dialkylphenanthrone derivatives. A possible reaction mechanism involving directed dual C-H bond activation and enolate cyclization for the formation of 10,10-dialkylphenanthrone derivatives is proposed.

摘要

钯催化的烷基芳基酮的螯合辅助 C-H 活化及其与芳基碘化物的反应,以提供邻芳基化产物被描述。对于 sec-烷基芳基酮,催化反应进一步进行,得到 10,10-二烷基菲啶酮衍生物。提出了一种可能的反应机制,涉及定向双 C-H 键活化和烯醇环化,用于形成 10,10-二烷基菲啶酮衍生物。

相似文献

1
Synthesis of phenanthrone derivatives from sec-alkyl aryl ketones and aryl halides via a palladium-catalyzed dual C-H bond activation and enolate cyclization.通过钯催化的双重 C-H 键活化和烯醇环化反应,从仲烷基芳基酮和芳基卤化物合成菲并[9,10-d]恶嗪衍生物。
J Am Chem Soc. 2010 Jun 30;132(25):8569-71. doi: 10.1021/ja1026248.
2
Palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls.钯催化α,α-二取代芳基甲醇通过碳-碳或碳-氢键的断裂进行芳基化反应以生成联芳基化合物。
J Org Chem. 2003 Jun 27;68(13):5236-43. doi: 10.1021/jo0344034.
3
Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents.钯-次膦酸催化芳基和酰基卤化物与芳基、烷基和乙烯基锌试剂的交叉偶联反应。
J Org Chem. 2008 Oct 3;73(19):7638-50. doi: 10.1021/jo801445y. Epub 2008 Sep 4.
4
Palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides leading to alkyl aryl ketones.钯催化的三烷基胺与芳基碘的氧化偶联反应生成芳基烷基酮。
Org Lett. 2011 May 6;13(9):2184-7. doi: 10.1021/ol200404z. Epub 2011 Apr 7.
5
Tuned C-H functionalization to construct aza-podophyllotoxin/aza-conidendrin derivatives by means of domino cyclization.通过多米诺环化反应,调谐 C-H 功能化构建氮杂鬼臼毒素/氮杂柯坪脂衍生物。
Chem Asian J. 2010 Feb 1;5(2):309-14. doi: 10.1002/asia.200900307.
6
Catalytic sequential reactions involving palladacycle-directed aryl coupling steps.涉及钯环导向芳基偶联步骤的催化连续反应。
Acc Chem Res. 2008 Nov 18;41(11):1512-22. doi: 10.1021/ar800040u.
7
Pd0-catalyzed coupling cyclization reaction of Aryl or 1-alkenyl halides with 1,2-allenyl ketones: scope and mechanism. An efficient assembly of 2,3,4-, 2,3,5-tri- and 2,3,4,5-tetrasubstituted furans.钯(0)催化芳基或1-烯基卤化物与1,2-联烯基酮的偶联环化反应:范围与机理。2,3,4-、2,3,5-三取代及2,3,4,5-四取代呋喃的高效合成。
Chemistry. 2003 Jun 6;9(11):2447-56. doi: 10.1002/chem.200204664.
8
Palladium-catalyzed oxidative carbonylation of alkyl and aryl indium reagents with CO under mild conditions.钯催化的烷基和芳基铟试剂在温和条件下与一氧化碳的氧化羰基化反应。
J Am Chem Soc. 2008 Jul 23;130(29):9429-33. doi: 10.1021/ja801116s. Epub 2008 Jun 25.
9
Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones.钯催化(Z)-1-(1,3-丁二烯基)环丁醇与芳基碘的扩环反应。(Z)-2-(3-芳基-1-丙烯基)环戊酮的立体定向合成。
Org Lett. 2004 Jun 10;6(12):1979-82. doi: 10.1021/ol049438k.
10
Palladium-catalyzed carbonylative cycloisomerization of gamma-propynyl-1,3-diketones: a concise route to polysubstituted furans.钯催化γ-丙炔基-1,3-二酮的羰基环化异构化反应:多取代呋喃的简洁合成路线。
J Org Chem. 2009 Nov 20;74(22):8904-7. doi: 10.1021/jo9020634.

引用本文的文献

1
Palladium-Catalyzed C-H Arylation of Quinoidal Scaffolds Through Homogeneous and Heterogeneous Pathways: Advancing Toward Trypanocidal Prototypes.通过均相和非均相途径实现的钯催化醌类骨架的C-H芳基化:迈向抗锥虫原型
ACS Omega. 2025 Aug 14;10(33):37898-37905. doi: 10.1021/acsomega.5c05006. eCollection 2025 Aug 26.
2
Ring Expansion via Palladium-Catalyzed Aryne Insertion into C-C Bonds of Benzocyclobutenones.通过钯催化芳炔插入苯并环丁烯酮的碳-碳键实现环扩展
Angew Chem Int Ed Engl. 2025 Apr 25;64(18):e202500148. doi: 10.1002/anie.202500148. Epub 2025 Mar 2.
3
The Activating Effect of Strong Acid for Pd-Catalyzed Directed C-H Activation by Concerted Metalation-Deprotonation Mechanism.
强酸性对 Pd 催化协同金属化-去质子化机理导向的 C-H 活化的活化作用。
Molecules. 2021 Jul 4;26(13):4083. doi: 10.3390/molecules26134083.
4
Theoretical studies on the mechanism of Pd-catalyzed regioselective C-H alkylation of indole with MesICHCFOTf.钯催化吲哚与 MesICHCFOTf 的区域选择性 C-H 烷基化反应机理的理论研究。
J Mol Model. 2021 May 4;27(5):150. doi: 10.1007/s00894-021-04773-6.
5
Distal γ-C(sp )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.酮衍生物和游离羧酸的远端γ-C(sp )-H 烯烃化反应。
Angew Chem Int Ed Engl. 2020 Jul 27;59(31):12853-12859. doi: 10.1002/anie.202003271. Epub 2020 Jun 5.
6
Ligand-Enabled, Palladium-Catalyzed β-C(sp)-H Arylation of Weinreb Amides.配体促进的钯催化的N-甲氧基-N-甲基酰胺的β-C(sp)-H芳基化反应
ACS Catal. 2018 Oct 5;8(10):9292-9297. doi: 10.1021/acscatal.8b03014. Epub 2018 Sep 5.
7
C4-H indole functionalisation: precedent and prospects.C4-氢吲哚官能团化:先例与前景
Chem Sci. 2018 Apr 20;9(18):4203-4216. doi: 10.1039/c7sc05336c. eCollection 2018 May 14.
8
Ruthenium(η⁶,η¹-arene-CH₂-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water.钌(η⁶,η¹-芳基-CH₂-NHC)催化剂在水中对 2-苯基吡啶与(杂)芳基氯的直接芳基化反应。
Molecules. 2018 Mar 13;23(3):647. doi: 10.3390/molecules23030647.
9
Aromatic C-H addition of ketones to imines enabled by manganese catalysis.锰催化促进的酮与亚胺的芳基 C-H 加成反应。
Nat Commun. 2017 Oct 27;8(1):1169. doi: 10.1038/s41467-017-01262-4.
10
Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.由远端弱配位官能团导向的钯(II)催化的C-H官能化反应。
J Am Chem Soc. 2015 Apr 8;137(13):4391-7. doi: 10.1021/ja5126897. Epub 2015 Mar 24.