钯/降冰片烯协同催化
Palladium/Norbornene Cooperative Catalysis.
作者信息
Wang Jianchun, Dong Guangbin
机构信息
Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
出版信息
Chem Rev. 2019 Jun 26;119(12):7478-7528. doi: 10.1021/acs.chemrev.9b00079. Epub 2019 Apr 25.
Abstract
Palladium/norbornene cooperative catalysis has emerged as a distinct approach to construct polyfunctionalized arenes from readily available starting materials. This Review provides a comprehensive overview of this field, including the early stoichiometric investigations, catalytic reaction developments, as well as the applications in the syntheses of bioactive compounds and polymers. The section of catalytic reactions is divided into two parts according to the reaction initiation mode: Pd(0)-initiated reactions and Pd(II)-initiated reactions.
摘要
钯/降冰片烯协同催化已成为一种从易得的起始原料构建多官能化芳烃的独特方法。本综述全面概述了该领域，包括早期的化学计量研究、催化反应的发展，以及在生物活性化合物和聚合物合成中的应用。催化反应部分根据反应引发模式分为两部分：钯(0)引发的反应和钯(II)引发的反应。
相似文献
1
Palladium/Norbornene Cooperative Catalysis.钯/降冰片烯协同催化
Chem Rev. 2019 Jun 26;119(12):7478-7528. doi: 10.1021/acs.chemrev.9b00079. Epub 2019 Apr 25.
2
Entry to 1,2,3,4-Tetrasubstituted Arenes through Addressing the " Constraint" in the Palladium/Norbornene Catalysis.通过在钯/降冰片烯催化中解决“约束”来进入 1,2,3,4-四取代芳烃。
J Am Chem Soc. 2020 Feb 12;142(6):3050-3059. doi: 10.1021/jacs.9b12355. Epub 2020 Jan 30.
3
Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.结构修饰降冰片烯：调控钯/降冰片烯协同催化反应选择性的关键因素。
J Am Chem Soc. 2020 Oct 21;142(42):17859-17875. doi: 10.1021/jacs.0c09193. Epub 2020 Oct 5.
4
Sulfenamide-enabled ortho thiolation of aryl iodides via palladium/norbornene cooperative catalysis.钯/降冰片烯协同催化实现芳基碘的砜酰胺导向邻位硫代反应。
Nat Commun. 2019 Aug 7;10(1):3555. doi: 10.1038/s41467-019-11398-0.
5
Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.通过钯/降冰片烯协同催化实现芳基溴化物的模块间 ipso/ortho 双官能化反应。
J Am Chem Soc. 2018 Jul 11;140(27):8551-8562. doi: 10.1021/jacs.8b04153. Epub 2018 Jun 27.
6
Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis.钯/降冰片烯协同催化噻吩的直接邻位双官能化反应。
J Am Chem Soc. 2019 Dec 4;141(48):18958-18963. doi: 10.1021/jacs.9b10857. Epub 2019 Nov 22.
7
Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.钯/降冰片烯催化由简单芳基碘化物合成茚酮：简洁合成少花瑞香素F和阿克里德酮A。
Angew Chem Int Ed Engl. 2019 Feb 11;58(7):2144-2148. doi: 10.1002/anie.201813699. Epub 2019 Jan 16.
8
Modular Entry to Functionalized Tetrahydrobenzo[]azepines via the Palladium/Norbornene Cooperative Catalysis Enabled by a C7-Modified Norbornene.通过 C7 修饰的降冰片烯实现钯/降冰片烯协同催化的模块化进入功能化四氢苯并[a]氮杂卓
J Am Chem Soc. 2021 Jul 7;143(26):9991-10004. doi: 10.1021/jacs.1c04575. Epub 2021 Jun 23.
9
Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis.通过钯/降冰片烯协同催化实现远端烯基碳氢键官能团化
J Am Chem Soc. 2020 Feb 12;142(6):2715-2720. doi: 10.1021/jacs.9b11479. Epub 2020 Feb 3.
10
Ortho C-H Acylation of Aryl Iodides by Palladium/Norbornene Catalysis.钯/降冰片烯催化芳基碘的 C-H 酰化反应。
Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12664-8. doi: 10.1002/anie.201506397. Epub 2015 Sep 1.
引用本文的文献
1
Modular arene functionalization by differential 1,2-diborylation.通过差分1,2-二硼化实现模块化芳烃官能化
Nature. 2025 Aug;644(8075):102-108. doi: 10.1038/s41586-025-09284-5. Epub 2025 Jun 23.
2
Asymmetric total synthesis of benzenoid cephalotane-type diterpenoids through a cascade C(sp) & C(sp)-H activation.通过串联C(sp)和C(sp)-H活化实现苯并环戊烷型二萜类化合物的不对称全合成。
Nat Commun. 2025 May 20;16(1):4674. doi: 10.1038/s41467-025-59816-w.
3
Triple cross-electrophile coupling enabled by palladium/norbornene cooperative catalysis.钯/降冰片烯协同催化实现的三交叉亲电偶联反应。
Sci Adv. 2025 May 2;11(18):eadu4573. doi: 10.1126/sciadv.adu4573. Epub 2025 Apr 30.
4
Manipulating Electronic Effect of Nitrogen Donor-Based Ligands for Efficient Complexation and Separation of Palladium from Highly Acidic Solution.调控含氮供体配体的电子效应以实现钯在高酸性溶液中的高效络合与分离
Molecules. 2025 Mar 30;30(7):1533. doi: 10.3390/molecules30071533.
5
Concise Total Syntheses of Leuconoxine-Type Alkaloids Enabled by Palladium/Norbornene-Catalyzed Pyrrole Difunctionalization.钯/降冰片烯催化的吡咯双官能化实现亮氨酸型生物碱的简洁全合成
Angew Chem Int Ed Engl. 2025 Jun 2;64(23):e202502736. doi: 10.1002/anie.202502736. Epub 2025 Apr 10.
6
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.
7
Meta-Dimethylation of Arenes via Catellani Reaction from Aryl Thianthrenium Salts.通过芳基噻蒽鎓盐的卡泰拉尼反应实现芳烃的间位二甲基化
Angew Chem Int Ed Engl. 2025 Jan 27;64(5):e202419472. doi: 10.1002/anie.202419472. Epub 2024 Nov 25.
8
A switch strategy for the synthesis of C4-ethylamine indole and C7-aminoindoline controllable carbon elimination.一种用于合成C4-乙胺吲哚和C7-氨基二氢吲哚的可控碳消除的转换策略。
Chem Sci. 2024 Sep 6;15(39):16169-75. doi: 10.1039/d4sc05111d.
9
Chiral dinitrogen ligand enabled asymmetric Pd/norbornene cooperative catalysis toward the assembly of C-N axially chiral scaffolds.手性双氮配体实现了不对称钯/降冰片烯协同催化，用于构建C-N轴手性骨架。
Nat Commun. 2024 Jun 8;15(1):4908. doi: 10.1038/s41467-024-48582-w.
10
Enantioconvergent synthesis of chiral fluorenols from racemic secondary alcohols Pd(ii)/chiral norbornene cooperative catalysis.从外消旋仲醇对映汇聚式合成手性芴醇：钯（II）/手性降冰片烯协同催化
Chem Sci. 2024 Apr 25;15(21):7975-7981. doi: 10.1039/d4sc01004c. eCollection 2024 May 29.
本文引用的文献
1
Functionalized Rigid Ladder Polymers from Catalytic Arene-Norbornene Annulation Polymerization.通过催化芳烃-降冰片烯环化聚合反应制备的功能化刚性梯形聚合物。
ACS Macro Lett. 2017 Dec 19;6(12):1357-1361. doi: 10.1021/acsmacrolett.7b00806. Epub 2017 Nov 27.
2
Redox-Neutral Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis.通过钯/降冰片烯协同催化实现芳基硼酸酯的氧化还原中性官能团化
Chem. 2019 Apr 11;5(4):929-939. doi: 10.1016/j.chempr.2019.02.005. Epub 2019 Mar 7.
3
Palladium-catalyzed asymmetric annulation between aryl iodides and racemic epoxides using a chiral norbornene cocatalyst.使用手性降冰片烯助催化剂实现芳基碘化物与外消旋环氧化物之间的钯催化不对称环化反应。
Org Chem Front. 2018 Nov 7;5(21):3108-3112. doi: 10.1039/c8qo00808f. Epub 2018 Sep 25.
4
Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.钯/降冰片烯催化由简单芳基碘化物合成茚酮：简洁合成少花瑞香素F和阿克里德酮A。
Angew Chem Int Ed Engl. 2019 Feb 11;58(7):2144-2148. doi: 10.1002/anie.201813699. Epub 2019 Jan 16.
5
Palladium(II)-Initiated Catellani-Type Reactions.钯（II）引发的卡塔兰尼型反应。
Angew Chem Int Ed Engl. 2019 Apr 23;58(18):5832-5844. doi: 10.1002/anie.201813491. Epub 2019 Feb 20.
6
Palladium Catalyzed -C-H Functionalization of Masked Aromatic Aldehydes.钯催化的掩蔽芳香醛的-C-H官能化反应
ACS Catal. 2018 Aug 3;8(8):7362-7367. doi: 10.1021/acscatal.8b01599. Epub 2018 Jul 5.
7
Highly Chemoselective Construction of Spiro[4,5]decane-Embedded Polycyclic Scaffolds by a Palladium/Norbornene-Catalyzed C-H Activation/Arene Dearomatization Reaction.通过钯/降冰片烯催化的C-H活化/芳烃去芳构化反应高化学选择性构建含螺[4,5]癸烷的多环骨架
Org Lett. 2018 Dec 7;20(23):7731-7734. doi: 10.1021/acs.orglett.8b03518. Epub 2018 Nov 29.
8
Palladium/Norbornene Chemistry: Synthesis of Norbornene-Containing Arylsilanes Involving Double C-Si Bond Formation.钯/降冰片烯化学：涉及双C-Si键形成的含降冰片烯芳基硅烷的合成
J Org Chem. 2018 Nov 16;83(22):13930-13939. doi: 10.1021/acs.joc.8b02282. Epub 2018 Oct 25.
9
Expeditious Synthesis of 6-Fluoroalkyl-Phenanthridines via Palladium-Catalyzed Norbornene-Mediated Dehydrogenative Annulation.通过钯催化降冰片烯介导的脱氢环化反应快速合成 6-氟烷基菲啶。
Org Lett. 2018 Nov 2;20(21):6640-6645. doi: 10.1021/acs.orglett.8b02588. Epub 2018 Oct 15.
10
Pd(II)/Norbornene-Catalyzed Meta-C-H Alkylation of Nosyl-Protected Phenylalanines.Pd(II)/降冰片烯催化的对甲苯磺酰基保护苯丙氨酸的间-C-H 烷基化反应。
J Org Chem. 2018 Nov 2;83(21):13211-13216. doi: 10.1021/acs.joc.8b01933. Epub 2018 Oct 18.
Zotero 插件