镍催化去芳构化反式-1,2-碳酰胺化反应。
Nickel-Catalyzed Dearomative trans-1,2-Carboamination.
机构信息
Roger Adams Laboratory, Department of Chemistry , University of Illinois , Urbana , Illinois 61801 , United States.
出版信息
J Am Chem Soc. 2018 Apr 4;140(13):4503-4507. doi: 10.1021/jacs.8b01726. Epub 2018 Mar 23.
Abstract
We describe the development of an arenophile-mediated, nickel-catalyzed dearomative trans-1,2-carboamination protocol. A range of readily available aromatic compounds was converted to the corresponding dienes using Grignard reagents as nucleophiles. This strategy provided products with exclusive trans-selectivity and high enantioselectivity was observed in case of benzene and naphthalene. The utility of this methodology was showcased by controlled and stereoselective preparation of small, functionalized molecules.
摘要
我们描述了一种芳基亲核试剂介导的、镍催化的去芳构化反式-1,2-碳酰胺化反应的发展。一系列易得的芳族化合物被转化为相应的二烯，使用格氏试剂作为亲核试剂。这种策略提供了具有高反式选择性的产物，在苯和萘的情况下观察到高对映选择性。通过控制和立体选择性地制备小的、功能化的分子，展示了这种方法的实用性。
相似文献
1
Nickel-Catalyzed Dearomative trans-1,2-Carboamination.镍催化去芳构化反式-1,2-碳酰胺化反应。
J Am Chem Soc. 2018 Apr 4;140(13):4503-4507. doi: 10.1021/jacs.8b01726. Epub 2018 Mar 23.
2
Palladium-Catalyzed Dearomative syn-1,4-Carboamination.钯催化的去芳构化 syn-1,4-碳酰胺化反应。
J Am Chem Soc. 2017 Dec 13;139(49):17787-17790. doi: 10.1021/jacs.7b11663. Epub 2017 Dec 5.
3
Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.钯催化的与格氏试剂的去芳构化 syn-1,4-碳酰胺化反应。
Angew Chem Int Ed Engl. 2019 Jul 22;58(30):10245-10249. doi: 10.1002/anie.201905021. Epub 2019 Jun 24.
4
Palladium-Catalyzed Dearomative syn-1,4-Diamination.钯催化的去芳构化 syn-1,4-二氨基化反应。
J Am Chem Soc. 2019 Jan 9;141(1):163-167. doi: 10.1021/jacs.8b13030. Epub 2018 Dec 21.
5
Palladium-Catalyzed Dearomative syn-1,4-Oxyamination.钯催化的去芳构化 syn-1,4-氧氮杂环丙烷化反应。
Angew Chem Int Ed Engl. 2019 Oct 28;58(44):15762-15766. doi: 10.1002/anie.201909838. Epub 2019 Sep 20.
6
Stereospecific nickel-catalyzed cross-coupling reactions of benzylic ethers and esters.苄基醚和酯的立体选择性镍催化交叉偶联反应。
Acc Chem Res. 2015 Aug 18;48(8):2344-53. doi: 10.1021/acs.accounts.5b00223. Epub 2015 Jul 21.
7
Direct aminoalkylation of arenes, heteroarenes, and alkenes via Ni-catalyzed Negishi cross-coupling reactions.通过镍催化的 Negishi 交叉偶联反应实现芳基、杂芳基和烯烃的直接胺烷基化。
J Org Chem. 2011 Nov 4;76(21):8891-906. doi: 10.1021/jo201630e. Epub 2011 Oct 4.
8
Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp) Nucleophiles.镍催化的非环支化二烯与未稳定 C(sp3)亲核试剂的区域选择性和立体选择性氢烷基化反应。
J Am Chem Soc. 2020 Sep 23;142(38):16486-16492. doi: 10.1021/jacs.0c08319. Epub 2020 Sep 14.
9
Exploring new uses for C-H amination: Ni-catalyzed cross-coupling of cyclic sulfamates.探索C-H胺化的新用途：镍催化的环状氨基磺酸酯交叉偶联反应。
Org Lett. 2005 Oct 13;7(21):4685-8. doi: 10.1021/ol051896l.
10
Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C-H bond functionalization.镍催化的 N-芳杂环与格氏试剂的烷基化反应通过直接 C-H 键功能化实现。
Chem Commun (Camb). 2012 Jul 7;48(53):6717-9. doi: 10.1039/c2cc32396f. Epub 2012 May 24.
引用本文的文献
1
Palladium-catalyzed dearomative 1,4-hydroamination.钯催化的去芳构化1,4-氢胺化反应。
Tetrahedron. 2024 Aug 21;163. doi: 10.1016/j.tet.2024.134135. Epub 2024 Jul 4.
2
Enantioselective aza-electrophilic dearomatization of naphthalene derivatives.萘衍生物的对映选择性氮杂亲电去芳构化反应。
Nat Commun. 2025 Jul 1;16(1):5488. doi: 10.1038/s41467-025-60660-1.
3
Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.重新构想脱芳构化：亲芳烃介导的单原子插入和π扩展。
Acc Chem Res. 2025 Apr 1;58(7):1134-1150. doi: 10.1021/acs.accounts.5c00035. Epub 2025 Mar 11.
4
Copper-Catalyzed Dearomative -1,2-Carboamination.铜催化的去芳构化-1,2-碳胺化反应
ACS Catal. 2024 Jul 5;14(13):10132-10137. doi: 10.1021/acscatal.4c02656. Epub 2024 Jun 20.
5
Photochemical dearomative skeletal modifications of heteroaromatics.杂芳烃的光化学脱芳构化骨架修饰
Chem Soc Rev. 2024 Jun 17;53(12):6600-6624. doi: 10.1039/d4cs00137k.
6
Copper-Catalyzed Dearomative 1,2-Hydroamination.铜催化的去芳构化1,2-氢胺化反应
Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202407281. doi: 10.1002/anie.202407281. Epub 2024 Jul 16.
7
Switchable chemoselective aryne reactions between nucleophiles and pericyclic reaction partners using either 3-methoxybenzyne or 3-silylbenzyne.利用3-甲氧基苯炔或3-硅基苯炔在亲核试剂与周环反应伙伴之间进行的可切换化学选择性芳炔反应。
Nat Commun. 2024 Apr 30;15(1):3665. doi: 10.1038/s41467-024-47952-8.
8
Radical-Dearomative Generation of Cyclohexadienyl Pd(II) toward the 3D Transformation of Nonactivated Phenyl Rings.环己二烯基钯（II）对未活化苯环的3D转化的自由基脱芳构化生成
Adv Sci (Weinh). 2024 Mar;11(9):e2307074. doi: 10.1002/advs.202307074. Epub 2023 Dec 15.
9
π-Extended Rubrenes via Dearomative Annulative π-Extension Reaction.通过去芳构化环化 π-扩展反应构建 π-扩展鲁比烯。
J Am Chem Soc. 2023 Jan 11;145(1):658-666. doi: 10.1021/jacs.2c11338. Epub 2022 Dec 23.
10
Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization.利用有机光氧化还原去芳构化功能化选择性地编辑多环芳烃。
Nat Commun. 2022 Aug 5;13(1):4565. doi: 10.1038/s41467-022-32201-7.
本文引用的文献
1
Palladium-Catalyzed Dearomative syn-1,4-Carboamination.钯催化的去芳构化 syn-1,4-碳酰胺化反应。
J Am Chem Soc. 2017 Dec 13;139(49):17787-17790. doi: 10.1021/jacs.7b11663. Epub 2017 Dec 5.
2
Cu-Catalyzed Three-Component Carboamination of Alkenes.铜催化的烯烃三组分碳氨化反应。
J Am Chem Soc. 2018 Jan 10;140(1):58-61. doi: 10.1021/jacs.7b10529. Epub 2017 Dec 28.
3
Group 6 Dihapto-Coordinate Dearomatization Agents for Organic Synthesis.用于有机合成的 6 配位二齿螯合去芳构化试剂。
Chem Rev. 2017 Nov 22;117(22):13721-13755. doi: 10.1021/acs.chemrev.7b00480. Epub 2017 Oct 24.
4
Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.通过苯的催化去对称化合成（+）- Pancratistatins
J Am Chem Soc. 2017 Nov 8;139(44):15656-15659. doi: 10.1021/jacs.7b10351. Epub 2017 Oct 25.
5
Iron-Catalyzed Carboamination of Olefins: Synthesis of Amines and Disubstituted β-Amino Acids.铁催化烯烃的碳氨化反应：胺和二取代β-氨基酸的合成。
J Am Chem Soc. 2017 Sep 20;139(37):13076-13082. doi: 10.1021/jacs.7b06590. Epub 2017 Sep 8.
6
Highly Functionalized Tricyclic Oxazinanones via Pairwise Oxidative Dearomatization and N-Hydroxycarbamate Dehydrogenation: Molecular Diversity Inspired by Tetrodotoxin.通过成对的氧化去芳构化和 N-羟基氨基甲酸酯脱氢反应构建高功能化的三环氧化吗啉酮：受河豚毒素启发的分子多样性。
J Am Chem Soc. 2017 Sep 13;139(36):12422-12425. doi: 10.1021/jacs.7b07745. Epub 2017 Aug 30.
7
Sequential Tandem Addition to a Tungsten-Trifluorotoluene Complex: A Versatile Method for the Preparation of Highly Functionalized Trifluoromethylated Cyclohexenes.三氟甲基化环己烯的高官能团化制备：钨-三氟甲苯络合物的串联加成方法。
J Am Chem Soc. 2017 Aug 23;139(33):11401-11412. doi: 10.1021/jacs.7b05118. Epub 2017 Aug 14.
8
Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation.通过导向氨基钯化实现非活化烯烃的催化分子间碳氨化反应。
J Am Chem Soc. 2017 Aug 16;139(32):11261-11270. doi: 10.1021/jacs.7b06520. Epub 2017 Aug 4.
9
Chemoselective Asymmetric Intramolecular Dearomatization of Phenols with α-Diazoacetamides Catalyzed by Silver Phosphate.银磷酸盐催化的酚与α-重氮乙酰胺的化学选择性不对称分子内环化去芳构化反应。
J Am Chem Soc. 2017 Aug 2;139(30):10188-10191. doi: 10.1021/jacs.7b04813. Epub 2017 Jul 21.
10
Palladium-Catalyzed Cascade sp C-H Functionalization/Intramolecular Asymmetric Allylation: From Aryl Ureas and 1,3-Dienes to Chiral Indolines.钯催化的级联 sp3 C-H 功能化/分子内不对称烯丙基化：从芳基脲和 1,3-二烯到手性吲哚啉。
Angew Chem Int Ed Engl. 2017 Jun 1;56(23):6641-6645. doi: 10.1002/anie.201702745. Epub 2017 May 3.
Zotero 插件