• 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

一锅法通过光氧化和可调节的金属有机捕获亚胺中间体实现 N-取代的四氢异喹啉的功能化。

One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates.

机构信息

WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom ; GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom.

GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom.

出版信息

Beilstein J Org Chem. 2014 Dec 12;10:2981-8. doi: 10.3762/bjoc.10.316. eCollection 2014.

DOI:10.3762/bjoc.10.316
PMID:25550765
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4273301/
Abstract

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

摘要

通过氧化官能化叔胺生成的亚胺盐的亲核捕获已被广泛应用于稳定碳亲核试剂。少数关于有机金属加成的报道的底物和有机金属亲核试剂的适用范围有限。我们报告了一种新颖的一锅法方法，通过可见光辅助光氧化作用对 N-取代的四氢异喹啉进行功能化，然后用有机金属亲核试剂捕获所得的亚胺离子。该方法以中等至优秀的收率得到 1,2-二取代的四氢异喹啉。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/0acc0ec6d1c9/Beilstein_J_Org_Chem-10-2981-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/8cba609a0d87/Beilstein_J_Org_Chem-10-2981-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/d2acea662717/Beilstein_J_Org_Chem-10-2981-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/0b6f5ac9bc81/Beilstein_J_Org_Chem-10-2981-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/71729a5e0e41/Beilstein_J_Org_Chem-10-2981-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/3b95da17bf24/Beilstein_J_Org_Chem-10-2981-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/0acc0ec6d1c9/Beilstein_J_Org_Chem-10-2981-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/8cba609a0d87/Beilstein_J_Org_Chem-10-2981-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/d2acea662717/Beilstein_J_Org_Chem-10-2981-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/0b6f5ac9bc81/Beilstein_J_Org_Chem-10-2981-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/71729a5e0e41/Beilstein_J_Org_Chem-10-2981-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/3b95da17bf24/Beilstein_J_Org_Chem-10-2981-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51bc/4273301/0acc0ec6d1c9/Beilstein_J_Org_Chem-10-2981-g007.jpg

相似文献

1
One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates.一锅法通过光氧化和可调节的金属有机捕获亚胺中间体实现 N-取代的四氢异喹啉的功能化。
Beilstein J Org Chem. 2014 Dec 12;10:2981-8. doi: 10.3762/bjoc.10.316. eCollection 2014.
2
Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light.利用可见光生成的亚胺中间体的功能多样的亲核捕获。
Org Lett. 2012 Jan 6;14(1):94-7. doi: 10.1021/ol202883v. Epub 2011 Dec 8.
3
Regiospecific α-methylene functionalisation of tertiary amines with alkynes via Au-catalysed concerted one-proton/two-electron transfer to O.通过 Au 催化的协同质子/两电子转移到 O，实现炔烃对叔胺的区域选择性 α-亚甲基官能化。
Nat Commun. 2022 Nov 9;13(1):6505. doi: 10.1038/s41467-022-34176-x.
4
CuI-catalyzed C1-alkynylation of tetrahydroisoquinolines (THIQs) by A3 reaction with tunable iminium ions.铜催化四氢异喹啉（THIQs）通过 A3 反应与可调变亚胺离子的 C1-炔基化反应。
Org Lett. 2013 Dec 6;15(23):5928-31. doi: 10.1021/ol402517e. Epub 2013 Nov 15.
5
Investigating the Oxidation Step in the CuCl-Catalyzed Aerobic Oxidative Coupling Reaction of -Aryl Tetrahydroisoquinolines.研究 CuCl 催化 -芳基四氢异喹啉的有氧氧化偶联反应中的氧化步骤。
J Org Chem. 2020 Feb 21;85(4):1972-1980. doi: 10.1021/acs.joc.9b02707. Epub 2020 Jan 9.
6
Direct sp(3)C-H acroleination of N-aryl-tetrahydroisoquinolines by merging photoredox catalysis with nucleophilic catalysis.通过将光氧化还原催化与亲核催化相结合实现N-芳基四氢异喹啉的直接sp(3)C-H丙烯醛化反应。
Org Biomol Chem. 2014 Apr 7;12(13):2037-40. doi: 10.1039/c3ob42453g. Epub 2014 Feb 20.
7
Preparation of tertiary amines by the reaction of iminium ions derived from unsymmetrical aminals with zinc and magnesium organometallics.通过不对称亚胺与锌和镁有机金属反应制备叔胺。
Org Lett. 2015 Apr 17;17(8):2026-9. doi: 10.1021/acs.orglett.5b00801. Epub 2015 Apr 7.
8
Asymmetric catalytic formation of quaternary carbons by iminium ion trapping of radicals.不对称催化通过自由基捕获亚铵离子形成季碳。
Nature. 2016 Apr 14;532(7598):218-22. doi: 10.1038/nature17438.
9
Visible Light Driven Metal-Free Photoredox Catalyzed α-benzylation and α-oxygenation of N-substituted Tetrahydroisoquinolines: Applications to Synthesis of Natural Products.可见光驱动无金属光氧化还原催化 N-取代的四氢异喹啉的α-苄基化和α-氧化：在天然产物合成中的应用。
Chem Asian J. 2022 Nov 16;17(22):e202200878. doi: 10.1002/asia.202200878. Epub 2022 Sep 22.
10
Visible-light-induced direct C(sp3)-H difluromethylation of tetrahydroisoquinolines with the in situ generated difluoroenolates.可见光诱导的四氢异喹啉与原位生成的二氟烯醇化物的直接C(sp3)-H二氟甲基化反应。
Chem Commun (Camb). 2014 Jul 18;50(56):7521-3. doi: 10.1039/c4cc02768j.

引用本文的文献

1
An organophotocatalytic late-stage N-CH oxidation of trialkylamines to -formamides with O in continuous flow.一种在连续流动条件下，通过有机光催化实现三烷基胺的后期N-CH氧化以生成甲酰胺的方法，该过程使用氧气。
Chem Sci. 2021 Dec 28;13(7):1912-1924. doi: 10.1039/d1sc05840a. eCollection 2022 Feb 16.
2
Photoredox-Catalyzed C-H Functionalization Reactions.光氧化还原催化的 C-H 功能化反应。
Chem Rev. 2022 Jan 26;122(2):1925-2016. doi: 10.1021/acs.chemrev.1c00311. Epub 2021 Sep 29.
3
Regio- and chemoselective Csp-H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis.

本文引用的文献

1
Amine α-heteroarylation photoredox catalysis: a homolytic aromatic substitution pathway.胺α-杂芳基化光氧化还原催化：一种均裂芳香取代途径。
Chem Sci. 2014 Nov;5(11):4173-4178. doi: 10.1039/C4SC02155J.
2
Direct sp3 C-H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(III) under mild conditions.在温和条件下，高价碘（III）介导的四氢异喹啉的直接sp3 C-H键芳基化、烷基化和酰胺化反应。
Org Biomol Chem. 2014 Apr 14;12(14):2189-92. doi: 10.1039/c3ob42354a.
3
Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.
通过单电子转移/氢原子转移协同催化实现苄胺的区域和化学选择性Csp-H芳基化反应。
Chem Sci. 2018 Sep 12;9(44):8453-8460. doi: 10.1039/c8sc02965b. eCollection 2018 Nov 28.
4
Copper-catalyzed asymmetric sp C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst.可见光光氧化还原催化剂介导的铜催化四氢异喹啉的不对称sp C-H芳基化反应
Beilstein J Org Chem. 2016 Dec 6;12:2636-2643. doi: 10.3762/bjoc.12.260. eCollection 2016.
β-氨基酯对映选择性双催化合成中的光氧化还原活化与阴离子结合催化
Chem Sci. 2014 Jan;5(1). doi: 10.1039/C3SC52265B.
4
CuI-catalyzed C1-alkynylation of tetrahydroisoquinolines (THIQs) by A3 reaction with tunable iminium ions.铜催化四氢异喹啉（THIQs）通过 A3 反应与可调变亚胺离子的 C1-炔基化反应。
Org Lett. 2013 Dec 6;15(23):5928-31. doi: 10.1021/ol402517e. Epub 2013 Nov 15.
5
The chemistry of amine radical cations produced by visible light photoredox catalysis.可见光光氧化还原催化产生的胺自由基阳离子的化学。
Beilstein J Org Chem. 2013 Oct 1;9:1977-2001. doi: 10.3762/bjoc.9.234.
6
Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation under mild conditions.温和条件下通过 2,3-二氯-5,6-二氰基-1,4-苯醌氧化实现四氢异喹啉和异色满的 sp3 C-H 键芳基化反应，过程简单直接。
Org Lett. 2013 Jul 19;15(14):3650-3. doi: 10.1021/ol401534g. Epub 2013 Jul 1.
7
1-Methyl-1,2,3,4-tetrahydroisoquinoline, an endogenous amine with unexpected mechanism of action: new vistas of therapeutic application.1-甲基-1,2,3,4-四氢异喹啉，一种具有意外作用机制的内源性胺：治疗应用的新视角。
Neurotox Res. 2014 Jan;25(1):1-12. doi: 10.1007/s12640-013-9402-7. Epub 2013 May 30.
8
Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.布朗斯特酸共催化剂在光催化自由基加成α-氨基 C-H 键与迈克尔受体的反应中。
J Org Chem. 2013 Apr 19;78(8):4107-14. doi: 10.1021/jo400428m. Epub 2013 Apr 10.
9
Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.过渡金属配合物可见光光氧化还原催化：在有机合成中的应用
Chem Rev. 2013 Jul 10;113(7):5322-63. doi: 10.1021/cr300503r. Epub 2013 Mar 19.
10
A versatile C-H functionalization of tetrahydroisoquinolines catalyzed by iodine at aerobic conditions.在有氧条件下碘催化的四氢异喹啉的多功能 C-H 官能化。
Org Lett. 2013 Mar 1;15(5):1092-5. doi: 10.1021/ol4001153. Epub 2013 Feb 18.