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光氧化还原催化:通过烷氧基羰化/加成/环化序列构建多杂环。

Photoredox Catalysis: Construction of Polyheterocycles via Alkoxycarbonylation/Addition/Cyclization Sequence.

机构信息

School of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing Normal University , Nanjing 210023, China.

出版信息

Org Lett. 2017 Jul 7;19(13):3580-3583. doi: 10.1021/acs.orglett.7b01553. Epub 2017 Jun 28.

DOI:10.1021/acs.orglett.7b01553
PMID:28656766
Abstract

A novel visible-light-induced cascade reaction for the preparation of ester-functionalized polyheterocycles was developed under metal-free conditions, which was initiated by an intermolecular radical addition to a carbon-carbon double bond of N-arylacrylamide derivatives using alkyl carbazate as the ester source followed by cyano-mediated cyclization. The desired phenanthridine derivative products were isolated in moderate to high yields with broad substrate scope.

摘要

发展了一种新型的可见光诱导级联反应,用于在无金属条件下制备酯基功能化的多杂环化合物,该反应通过烷基碳二亚胺作为酯源与 N-芳基丙烯酰胺衍生物的碳-碳双键进行分子间自由基加成,然后通过氰基介导的环化来引发。以中等至高产率和广泛的底物范围分离得到所需的菲啶衍生物产物。

相似文献

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Photoredox Catalysis: Construction of Polyheterocycles via Alkoxycarbonylation/Addition/Cyclization Sequence.光氧化还原催化:通过烷氧基羰化/加成/环化序列构建多杂环。
Org Lett. 2017 Jul 7;19(13):3580-3583. doi: 10.1021/acs.orglett.7b01553. Epub 2017 Jun 28.
2
Visible-Light-Mediated Decarboxylative Alkylation Cascade Cyano Insertion/Cyclization of N-Arylacrylamides under Transition-Metal-Free Conditions.可见光促进的无金属条件下 N-芳基丙烯酰胺的脱羧烷基化级联氰基插入/环化反应。
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Visible-Light-Promoted Cyanoalkylation/Cyclization Cascade Reaction to Assemble Polyheterocycles in Continuous Flow.可见光促进的氰基烷基化/环化级联反应在连续流中组装多杂环化合物。
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Radical Addition/Insertion/Cyclization Cascade Reaction To Assemble Phenanthridines from N-Arylacrylamide Using Cyano as a Bridge under Photoredox Catalysis.光氧化还原催化下氰基桥联 N-芳基丙烯酰胺的自由基加成/插入/环化级联反应构建菲啶。
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Synthesis of trifluoroalkyl or difluoroalkyl phenanthridine derivatives via cascade reaction using an intramolecular cyano group as a radical acceptor under photoredox catalysis.通过光氧化还原催化,利用分子内氰基作为自由基受体,通过级联反应合成三氟烷基或二氟烷基菲啶衍生物。
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Metal-Free Photoredox Catalyzed Cyclization of O-(2,4-Dinitrophenyl)oximes to Phenanthridines.无金属光氧化还原催化O-(2,4-二硝基苯基)肟环化生成菲啶
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Silyl radical initiated radical cascade addition/cyclization: synthesis of silyl functionalized 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-ones.硅自由基引发的自由基级联加成/环化反应:硅基功能化 4H-吡啶并[4,3,2-gh]菲啶-5(6H)-酮的合成。
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引用本文的文献

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Synthesis of Ester-Containing Chroman-4-Ones via Cascade Radical Annulation of 2-(Allyloxy)Arylaldehydes with Oxalates under Metal Free Conditions.无金属条件下通过 2-(烯丙氧基)芳醛与草酸盐的级联自由基环化合成含酯基色满-4-酮。
Int J Mol Sci. 2023 Mar 6;24(5):5028. doi: 10.3390/ijms24055028.
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Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review.菲及其氮杂类似物的光催化合成。综述。
Beilstein J Org Chem. 2020 Jun 25;16:1476-1488. doi: 10.3762/bjoc.16.123. eCollection 2020.
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Recent Advances on Metal-Free, Visible-Light- Induced Catalysis for Assembling Nitrogen- and Oxygen-Based Heterocyclic Scaffolds.
无金属、可见光诱导催化在组装含氮和含氧杂环骨架中的最新进展。
Molecules. 2019 Apr 18;24(8):1533. doi: 10.3390/molecules24081533.
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Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay.铜催化的通过亚胺自由基的分子间阴离子自由基氧化还原接力的氧化苄位 C-H 环化反应。
Nat Commun. 2019 Feb 22;10(1):908. doi: 10.1038/s41467-019-08849-z.