钯催化中氮茚的芳基化和杂芳基化反应。
Palladium-catalyzed arylation and heteroarylation of indolizines.
作者信息
Park Choul-Hong, Ryabova Victoria, Seregin Ilya V, Sromek Anna W, Gevorgyan Vladimir
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor St, Chicago, Illinois 60607-7061, USA.
出版信息
Org Lett. 2004 Apr 1;6(7):1159-62. doi: 10.1021/ol049866q.
Abstract
A highly effective protocol for palladium-catalyzed selective arylation and heteroarylation of indolizines at C-3 has been developed. Mechanistic studies unambiguously support an electrophilic substitution pathway for this transformation.
摘要
已开发出一种高效的钯催化中氮茚在C-3位的选择性芳基化和杂芳基化反应方案。机理研究明确支持该转化过程的亲电取代途径。
相似文献
1
Palladium-catalyzed arylation and heteroarylation of indolizines.钯催化中氮茚的芳基化和杂芳基化反应。
Org Lett. 2004 Apr 1;6(7):1159-62. doi: 10.1021/ol049866q.
2
Synthesis of 3-aryl-8-oxo-5,6,7,8-tetrahydroindolizines via a palladium-catalyzed arylation and heteroarylation.通过钯催化的芳基化和杂芳基化反应合成3-芳基-8-氧代-5,6,7,8-四氢中氮茚
J Org Chem. 2009 Apr 17;74(8):3160-3. doi: 10.1021/jo802768n.
3
Direct palladium-catalyzed arylation of cyclopropenes.环丙烯的直接钯催化芳基化反应
J Am Chem Soc. 2005 Mar 23;127(11):3714-5. doi: 10.1021/ja042380k.
4
Direct palladium-catalyzed arylations of aryl bromides with 2/9-substituted pyrimido[5,4-b]indolizines.钯直接催化芳基溴化物与2/9-取代嘧啶并[5,4-b]中氮茚的芳基化反应。
J Comb Chem. 2009 Sep-Oct;11(5):806-8. doi: 10.1021/cc800162k.
5
Heteroarylation of Congested α-Bromoamides with Imidazo-Heteroarenes and Indolizines via Aza-Oxyallyl Cations: Enroute to Dibenzoazepinone and Zolpidem Analogues.通过氮杂烯丙基阳离子与咪唑杂芳环和吲哚嗪的拥挤 α-溴酰胺的杂芳基化反应：通向二苯并氮杂䓬酮和唑吡坦类似物。
J Org Chem. 2022 Nov 4;87(21):14168-14176. doi: 10.1021/acs.joc.2c01708. Epub 2022 Oct 19.
6
Palladium-catalyzed carbonylative cyclization/arylation cascade for 2-aroylindolizine synthesis.钯催化的羰基环化/芳基化级联反应合成 2-酰基吲哚嗪。
Org Lett. 2012 Dec 7;14(23):6056-9. doi: 10.1021/ol302947r. Epub 2012 Nov 28.
7
Palladium-catalyzed arylation and heteroarylation of azolopyrimidines.钯催化的唑并嘧啶的芳基化和杂芳基化反应。
J Org Chem. 2006 Feb 3;71(3):1254-7. doi: 10.1021/jo051848e.
8
Palladium-Catalyzed Arylation/Heteroarylation of Indoles: Access to 2,3-Functionalized Indolines.钯催化吲哚的芳基化/杂芳基化反应：2,3-二取代吲哚的合成。
Org Lett. 2018 Nov 16;20(22):7332-7335. doi: 10.1021/acs.orglett.8b03310. Epub 2018 Nov 7.
9
Direct palladium-catalyzed C-2 and C-3 arylation of indoles: a mechanistic rationale for regioselectivity.钯直接催化吲哚的C-2和C-3芳基化反应：区域选择性的机理依据
J Am Chem Soc. 2005 Jun 8;127(22):8050-7. doi: 10.1021/ja043273t.
10
Direct access to pyrazolo(benzo)thienoquinolines. Highly effective palladium catalysts for the intramolecular C-H heteroarylation of arenes.直接通往吡唑并[苯并]噻吩并喹啉。用于芳烃分子内 C-H 杂芳基化反应的高效钯催化剂。
Chem Commun (Camb). 2013 Feb 18;49(14):1413-5. doi: 10.1039/c2cc37905h.
引用本文的文献
1
Palladium-supported FeO@SiO functionalized methyl 2-phenyl thioacetate as a sustainable catalyst for Isatins synthesis.钯负载的FeO@SiO功能化的2-苯基硫代乙酸甲酯作为一种用于合成异吲哚酮的可持续催化剂。
Sci Rep. 2025 May 15;15(1):16918. doi: 10.1038/s41598-025-00775-z.
2
Palladium(II)-catalyzed annulation of N-methoxy amides and arynes: computational mechanistic insights and substituents effects.钯（II）催化的N-甲氧基酰胺与芳炔的环化反应：计算机理见解及取代基效应
J Mol Model. 2024 Apr 30;30(5):152. doi: 10.1007/s00894-024-05930-3.
3
Opening a Pandora's Flask on a Prototype Catalytic Direct Arylation Reaction of Pentafluorobenzene: The AgCO/Pd(OAc)/PPh System.开启潘多拉之瓶：五氟苯原型催化直接芳基化反应中的AgCO/Pd(OAc)/PPh体系
Organometallics. 2023 Aug 30;42(17):2378-2394. doi: 10.1021/acs.organomet.3c00309. eCollection 2023 Sep 11.
4
Metal-free visible-induced C(sp)-C(sp) coupling of quinoxalin-2()-ones oxidative cleavage of the C-N bond.喹喔啉-2（1H）-酮的无金属可见光诱导C（sp）-C（sp）偶联——C-N键的氧化裂解
RSC Adv. 2023 Jun 16;13(27):18328-18331. doi: 10.1039/d3ra03479h. eCollection 2023 Jun 15.
5
Mechanistic studies of the palladium-catalyzed S,O-ligand promoted C-H olefination of aromatic compounds.钯催化的S，O-配体促进芳香族化合物C-H烯基化反应的机理研究
Chem Sci. 2023 Feb 16;14(11):2943-2953. doi: 10.1039/d2sc06840k. eCollection 2023 Mar 15.
6
Rational ligand modification maximizes turnover rate in a model Pd-catalyzed C-H arylation.合理的配体修饰可使模型钯催化的C-H芳基化反应的转化率最大化。
iScience. 2022 Dec 10;26(1):105790. doi: 10.1016/j.isci.2022.105790. eCollection 2023 Jan 20.
7
Ligand-free Pd/Ag-mediated dehydrogenative alkynylation of imidazole derivatives.无配体钯/银介导的咪唑衍生物脱氢炔基化反应
RSC Adv. 2021 Jul 22;11(41):25504-25509. doi: 10.1039/d1ra05303e. eCollection 2021 Jul 19.
8
Direct Arylation in the Presence of Palladium Pincer Complexes.钯钳形配合物存在下的直接芳基化反应。
Molecules. 2021 Jul 20;26(14):4385. doi: 10.3390/molecules26144385.
9
Oligothiophene Synthesis by a General C-H Activation Mechanism: Concerted Metalation-Deprotonation (CMD).通过通用的C-H活化机制合成寡聚噻吩：协同金属化-去质子化（CMD）。
ACS Catal. 2019 Aug 2;9(8):6821-6836. doi: 10.1021/acscatal.9b01195. Epub 2019 Jun 24.
10
Donor-Acceptor-Donor Thienopyrazines via Pd-Catalyzed C-H Activation as NIR Fluorescent Materials.通过钯催化的C-H活化制备供体-受体-供体噻吩并吡嗪作为近红外荧光材料
J Org Chem. 2016 Jan 4;81(1):32-42. doi: 10.1021/acs.joc.5b01958. Epub 2015 Dec 11.
本文引用的文献
1
Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization.使用新型钯催化环化反应简洁全合成（-）-蕨叶霉素B
Angew Chem Int Ed Engl. 2002 May 3;41(9):1569-72. doi: 10.1002/1521-3773(20020503)41:9<1569::aid-anie1569>3.0.co;2-8.
2
Palladium-catalyzed regioselective arylation of imidazo[1,2-a]pyrimidine.钯催化的咪唑并[1,2 - a]嘧啶的区域选择性芳基化反应
Org Lett. 2003 Dec 11;5(25):4835-7. doi: 10.1021/ol035878k.
3
Indolizines as novel potent inhibitors of 15-lipoxygenase.吲哚嗪作为15-脂氧合酶的新型强效抑制剂。
Bioorg Med Chem. 2003 Dec 1;11(24):5409-15. doi: 10.1016/j.bmc.2003.09.033.
4
Diversity synthesis via C-H bond functionalization: concept-guided development of new C-arylation methods for imidazoles.通过C-H键官能团化实现多样性合成：咪唑新的C-芳基化方法的概念导向开发
J Am Chem Soc. 2003 Sep 3;125(35):10580-5. doi: 10.1021/ja036157j.
5
Selective C-arylation of free (NH)-heteroarenes via catalytic C-H bond functionalization.通过催化C-H键官能团化实现游离（NH）-杂芳烃的选择性C-芳基化。
J Am Chem Soc. 2003 May 7;125(18):5274-5. doi: 10.1021/ja034848+.
6
Isotope effects in C-H bond activation reactions by transition metals.过渡金属催化C-H键活化反应中的同位素效应
Acc Chem Res. 2003 Feb;36(2):140-6. doi: 10.1021/ar020148i.
7
Regioselective palladium-catalyzed arylation of 3-carboalkoxy furan and thiophene.钯催化的3-烷氧羰基呋喃和噻吩的区域选择性芳基化反应
Org Lett. 2003 Feb 6;5(3):301-4. doi: 10.1021/ol027266q.
8
Quinoline, quinazoline and acridone alkaloids.喹啉、喹唑啉和吖啶酮生物碱。
Nat Prod Rep. 2002 Dec;19(6):742-60. doi: 10.1039/b104971m.
9
Double cycloisomerization as a novel and expeditious route to tricyclic heteroaromatic compounds: short and highly diastereoselective synthesis of (+/-)-tetraponerine T6.双环异构化：一种合成三环杂芳族化合物的新颖且快速的途径——（±）-四环彭纳林T6的简短且高非对映选择性合成
Org Lett. 2002 Dec 26;4(26):4697-9. doi: 10.1021/ol027129t.
10
Probing opioid receptor interactions with azacycloalkane amino acids. Synthesis of a potent and selective ORL1 antagonist.探索阿片受体与氮杂环烷氨基酸的相互作用。一种强效且选择性的孤啡肽受体1拮抗剂的合成。
J Med Chem. 2002 Nov 21;45(24):5353-7. doi: 10.1021/jm020078l.
Zotero 插件