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可见光诱导3,4-二氢喹喔啉-2(1)-酮与亲核试剂发生C-C键形成反应，该反应可使用光氧化还原催化剂或在无催化剂条件下借助氧气进行。

Visible-light-induced C(sp)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions.

作者信息

Akula Pavan Sudheer, Hong Bor-Cherng, Lee Gene-Hsiang

机构信息

Department of Chemistry and Biochemistry, National Chung Cheng University Chia-Yi 621 Taiwan Republic of China

Instrumentation Center, National Taiwan University Taipei 106 Taiwan.

出版信息

RSC Adv. 2018 May 29;8(35):19580-19584. doi: 10.1039/c8ra03259a. eCollection 2018 May 25.

DOI:10.1039/c8ra03259a
PMID:35540997
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9080698/
Abstract

A convenient photocatalyzed oxidative coupling reaction of 4-alkyl-3,4-dihydroquinoxalin-2(1)-one and its derivatives with a variety of nucleophiles was developed with a ruthenium photoredox catalyst and oxygen under a household compact fluorescent light. With a slower reaction rate, the cross coupling transformation can be achieved in the absence of an external photocatalyst with a similar isolated yield. An application to the synthesis of natural product cephalandole A was also demonstrated.

摘要

利用钌光氧化还原催化剂和氧气，在家用紧凑型荧光灯下，开发了一种4-烷基-3,4-二氢喹喔啉-2(1)-酮及其衍生物与多种亲核试剂的便捷光催化氧化偶联反应。在没有外部光催化剂的情况下，以较慢的反应速率也能实现交叉偶联转化，且分离产率相似。还展示了该反应在天然产物头盘菌素A合成中的应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/3d69763d17a7/c8ra03259a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/8ddd16617de5/c8ra03259a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/3193abf5d974/c8ra03259a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/ec1c3d8087c8/c8ra03259a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/100dc7076209/c8ra03259a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/3d69763d17a7/c8ra03259a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/8ddd16617de5/c8ra03259a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/3193abf5d974/c8ra03259a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/ec1c3d8087c8/c8ra03259a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/100dc7076209/c8ra03259a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57d9/9080698/3d69763d17a7/c8ra03259a-s3.jpg

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Org Lett. 2018 Apr 6;20(7):2051-2054. doi: 10.1021/acs.orglett.8b00597. Epub 2018 Mar 21.
2
Visible-Light-Mediated Radical Arylation of Anilines with Acceptor-Substituted (Hetero)aryl Halides.可见光促进的芳基卤代物与取代苯胺的自由基芳基化反应。
Org Lett. 2017 Nov 3;19(21):5976-5979. doi: 10.1021/acs.orglett.7b03001.
3
Silver-catalyzed decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo-carboxylic acids.
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Molecules. 2020 Nov 12;25(22):5270. doi: 10.3390/molecules25225270.
银催化喹喔啉-2(1H)-酮与α-氧代羧酸的脱羧酰化反应
Org Biomol Chem. 2017 Oct 31;15(42):8929-8935. doi: 10.1039/c7ob02187a.
4
Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light.受光照驱动的无需催化剂和氧化还原中性的芳基三氟甲基化和烷基化反应。
J Am Chem Soc. 2017 Oct 11;139(40):14315-14321. doi: 10.1021/jacs.7b08685. Epub 2017 Oct 1.
5
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J Org Chem. 2017 Oct 20;82(20):11247-11252. doi: 10.1021/acs.joc.7b01930. Epub 2017 Oct 6.
6
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7
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Chem Commun (Camb). 2017 Jul 25;53(60):8482-8485. doi: 10.1039/c7cc03693k.
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Org Lett. 2017 Jul 7;19(13):3386-3389. doi: 10.1021/acs.orglett.7b01230. Epub 2017 Jun 22.