钯催化的 3-(2-碘苄基)-吲哚的级联碳钯化-环化反应，生成稠合的 6/5/7/6-和 6/5/5/6-杂环体系。
Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.
机构信息
Department of Chemistry, University of Illinois, 845 West Taylor Street, Chicago, IL 60607, USA.
出版信息
Chem Commun (Camb). 2010 Jan 7;46(1):150-2. doi: 10.1039/b919991h. Epub 2009 Nov 17.
Abstract
Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation-annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et(3)N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.
摘要
多环吲哚结构，具有稠合的七元环，可通过 Pd 催化的 3-(2-碘苄基)-吲哚和炔烃的分子内碳钯化-环化反应有效地合成。在这种转化的化学选择性方面发现了显著的碱效应：从 Et(3)N 切换到 CsOAc 完全改变了反应途径，形成了分子内环化，形成稠合的五元环。
相似文献
1
Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.钯催化的 3-(2-碘苄基)-吲哚的级联碳钯化-环化反应，生成稠合的 6/5/7/6-和 6/5/5/6-杂环体系。
Chem Commun (Camb). 2010 Jan 7;46(1):150-2. doi: 10.1039/b919991h. Epub 2009 Nov 17.
2
Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine.用于合成吲哚和中氮茚多环衍生物的级联碳钯化-环化方法。
ARKIVOC. 2010 Dec 10;2011(5):76-91.
3
Palladium-catalyzed intramolecular carbopalladation/cyclization cascade: access to polycyclic N-fused heterocycles.钯催化的分子内碳钯化/环化级联反应：多环 N 稠合杂环的构建。
Org Lett. 2010 Dec 3;12(23):5558-60. doi: 10.1021/ol102447s. Epub 2010 Nov 8.
4
Pd-catalyzed annulation of imidazo[1,2-]pyridines with coumarins and indoles: synthesis of benzofuran and indole fused heterocycles.钯催化的咪唑并[1,2-]吡啶与香豆素和吲哚的环化反应：苯并呋喃和吲哚稠合杂环的合成。
Chem Commun (Camb). 2022 Feb 1;58(10):1585-1588. doi: 10.1039/d1cc06803b.
5
Synthesis of Cyclohexane-Fused Isocoumarins via Cationic Palladium(II)-Catalyzed Cascade Cyclization Reaction of Alkyne-Tethered Carbonyl Compounds Initiated by Intramolecular Oxypalladation of Ester-Substituted Aryl Alkynes.通过酯取代芳基炔烃的分子内氧钯化引发的炔基羰基化合物的阳离子钯（II）催化级联环化反应合成环己烷稠合异香豆素。
J Org Chem. 2016 Apr 15;81(8):3423-9. doi: 10.1021/acs.joc.6b00128. Epub 2016 Mar 29.
6
Palladium-catalyzed domino process to spirooxindoles: ligand effect on aminopalladation versus carbopalladation.钯催化的多米诺反应合成螺氧化吲哚：配体对氨基钯化与碳钯化的影响
Chemistry. 2010 May 25;16(20):5863-7. doi: 10.1002/chem.201000312.
7
Pd(II)-catalyzed one-step construction of cycloalkane-fused indoles and its application in formal synthesis of (±)-aspidospermidine.Pd(II)催化的一步构建环烷并吲哚及其在(±)-阿朴斯皮定的形式合成中的应用。
Org Lett. 2014 Apr 4;16(7):2058-61. doi: 10.1021/ol500662f. Epub 2014 Mar 21.
8
One-pot synthesis of indole-fused scaffolds via gold-catalyzed tandem annulation reactions of 1,2-bis(alkynyl)-2-en-1-ones with indoles.一锅法合成吲哚并稠环骨架：金催化的 1,2-双（炔基）-2-烯-1-酮与吲哚的串联环化反应。
J Org Chem. 2011 Nov 4;76(21):9175-81. doi: 10.1021/jo2017668. Epub 2011 Oct 3.
9
Facile preparation of indoles and 1,2-benzothiazine 1,1-dioxides: nucleophilic addition of sulfonamides to bromoacetylenes and subsequent palladium-catalyzed cyclization.吲哚和 1,2-苯并噻嗪 1,1-二氧化物的简便制备：磺酰胺对溴代乙炔的亲核加成和随后的钯催化环化。
Angew Chem Int Ed Engl. 2012 Jun 25;51(26):6471-4. doi: 10.1002/anie.201201024. Epub 2012 May 13.
10
Fused ring construction around pyrrole, indole, and related compounds via palladium-catalyzed oxidative coupling with alkynes.通过钯催化的与炔烃的氧化偶联反应构建围绕吡咯、吲哚及相关化合物的稠环结构。
J Org Chem. 2009 Oct 2;74(19):7481-8. doi: 10.1021/jo9016698.
引用本文的文献
1
Advances in Selected Heterocyclization Methods.特定杂环化方法的进展
Synlett. 2023 Aug;34(13):1554-1562. doi: 10.1055/s-0042-1751429. Epub 2023 Mar 10.
2
New Reactions of Contraction of the -Quinone Ring with the Formation of Derivatives of 2-(2-Indolyl)-cyclopenta[b]pyrrole-3,4-diones and Pyrindino[1,2-a]indoles: A Combined Experimental and Density Functional Theory Investigation.醌环收缩形成2-(2-吲哚基)-环戊并[b]吡咯-3,4-二酮和吡啶并[1,2-a]吲哚衍生物的新反应：实验与密度泛函理论联合研究
ACS Omega. 2021 Jul 8;6(28):18226-18234. doi: 10.1021/acsomega.1c02033. eCollection 2021 Jul 20.
3
Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp C-H Bonds.钴催化、氨基喹啉导向的次膦酰胺sp C-H键官能化反应
ACS Catal. 2016 Feb 5;6(2):551-554. doi: 10.1021/acscatal.5b02391. Epub 2015 Dec 22.
4
Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.钴催化、氨基喹啉导向的炔烃对C(sp²)-H键的烯基化反应
Angew Chem Int Ed Engl. 2014 Sep 15;53(38):10209-12. doi: 10.1002/anie.201404579. Epub 2014 Jul 24.
5
Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine.用于合成吲哚和中氮茚多环衍生物的级联碳钯化-环化方法。
ARKIVOC. 2010 Dec 10;2011(5):76-91.
本文引用的文献
1
Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates.钯催化多种芳香底物直接芳基化反应中协同金属化-去质子化机理的分析
J Am Chem Soc. 2008 Aug 20;130(33):10848-9. doi: 10.1021/ja802533u. Epub 2008 Jul 29.
2
Anionic Indole N-carbamoyl N --> C translocation. A directed remote metalation route to 2-Aryl- and 2-heteroarylindoles. synthesis of benz[a]carbazoles and Indeno[1,2-b]indoles.阴离子吲哚N-甲酰基N→C迁移。通往2-芳基和2-杂芳基吲哚的定向远程金属化路线。苯并[a]咔唑和茚并[1,2-b]吲哚的合成。
Org Lett. 2008 Jul 3;10(13):2617-20. doi: 10.1021/ol800307g. Epub 2008 Jun 11.
3
Room temperature and phosphine free palladium catalyzed direct C-2 arylation of indoles.室温及无膦钯催化的吲哚直接C-2芳基化反应
J Am Chem Soc. 2008 Mar 12;130(10):2926-7. doi: 10.1021/ja710731a. Epub 2008 Feb 16.
4
Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.钯催化氧化芳烃交叉偶联反应中的区域控制要素
J Am Chem Soc. 2007 Oct 10;129(40):12072-3. doi: 10.1021/ja0745862. Epub 2007 Sep 19.
5
Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.简单吲哚生物碱以及具有未重排单萜单元的生物碱。
Nat Prod Rep. 2007 Aug;24(4):843-68. doi: 10.1039/b516351j. Epub 2007 Mar 23.
6
Direct transition metal-catalyzed functionalization of heteroaromatic compounds.直接过渡金属催化的杂芳族化合物官能化
Chem Soc Rev. 2007 Jul;36(7):1173-93. doi: 10.1039/b606984n. Epub 2007 Mar 5.
7
Synthesis of indolo[1,2-f]phenanthridines from palladium-catalyzed reactions of arynes.通过芳炔的钯催化反应合成吲哚并[1,2-f]菲啶
J Org Chem. 2007 Jul 6;72(14):5431-4. doi: 10.1021/jo070625g. Epub 2007 Jun 8.
8
Direct Pd-catalyzed arylation of 1,2,3-triazoles.钯直接催化的1,2,3-三唑芳基化反应
Org Lett. 2007 Jun 7;9(12):2333-6. doi: 10.1021/ol070697u. Epub 2007 May 10.
9
Proton-abstraction mechanism in the palladium-catalyzed intramolecular arylation: substituent effects.钯催化分子内芳基化反应中的质子夺取机理：取代基效应
J Am Chem Soc. 2007 May 30;129(21):6880-6. doi: 10.1021/ja071034a. Epub 2007 Apr 27.
10
Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides.钯催化富电子杂环与芳基氯化物的芳基化反应。
Org Lett. 2007 Apr 12;9(8):1449-51. doi: 10.1021/ol0702324. Epub 2007 Mar 15.
Zotero 插件