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可见光诱导、无过渡金属条件下氧化石墨烯促进吲哚 C3-杂化反应策略。

Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions.

机构信息

Department of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou 341000, China.

Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases of Ministry of Education, School of Pharmaceutical Science of Gannan Medical University, Ganzhou 341000, China.

出版信息

Molecules. 2022 Jan 25;27(3):772. doi: 10.3390/molecules27030772.

DOI:10.3390/molecules27030772
PMID:35164036
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8839487/
Abstract

An efficient and general method for the synthesis of 3-sulfenylindoles and 3-selenylindoles employing visible-light irradiation with graphene oxide as a promoter at room temperature has been achieved. The reaction features are high yields, simple operation, metal-free and iodine-free conditions, an easy-to-handle oxidant, and gram-scalable synthesis. This simple protocol allows one to access a wide range of 3-arylthioindoles, 3-arylselenylindoles, and even 3-thiocyanatoindoles with good to excellent yields.

摘要

采用氧化石墨烯作为促进剂,在室温下利用可见光照射,实现了一种高效、通用的 3-硫代吲哚和 3-硒代吲哚的合成方法。该反应具有产率高、操作简单、无需金属和碘、使用易于处理的氧化剂以及可规模化合成等特点。该简便的方法可用于合成各种 3-芳基硫代吲哚、3-芳基硒代吲哚,甚至 3-硫氰酸吲哚,产率良好至优秀。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/7aae658ea5a0/molecules-27-00772-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/18fdd25ae9ef/molecules-27-00772-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/fe85c9fdec23/molecules-27-00772-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/552bc306d211/molecules-27-00772-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/aa243ffe9759/molecules-27-00772-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/cd262b2d2a6a/molecules-27-00772-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/bb78db4897e5/molecules-27-00772-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/7aae658ea5a0/molecules-27-00772-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/18fdd25ae9ef/molecules-27-00772-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/fe85c9fdec23/molecules-27-00772-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/552bc306d211/molecules-27-00772-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/aa243ffe9759/molecules-27-00772-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/cd262b2d2a6a/molecules-27-00772-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/bb78db4897e5/molecules-27-00772-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/937a/8839487/7aae658ea5a0/molecules-27-00772-sch006.jpg

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本文引用的文献

1
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2
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Org Biomol Chem. 2019 Aug 14;17(30):7131-7134. doi: 10.1039/c9ob01340g. Epub 2019 Jul 16.
3
CoCl-promoted TEMPO oxidative homocoupling of indoles: access to tryptanthrin derivatives.
Top Curr Chem (Cham). 2024 Apr 12;382(2):13. doi: 10.1007/s41061-024-00460-1.
4
Low-Valent-Tungsten-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling Reaction.低价钨催化的需氧氧化交叉脱氢偶联反应
Molecules. 2023 Dec 13;28(24):8071. doi: 10.3390/molecules28248071.
CoCl 促进的 TEMPO 氧化吲哚同偶联反应:制备色胺酮衍生物。
Org Biomol Chem. 2018 Aug 8;16(31):5699-5706. doi: 10.1039/c8ob01216d.
4
Convenient synthesis of selenyl-indoles via iodide ion-catalyzed electrochemical C-H selenation.通过碘化离子催化电化学 C-H 硒化反应方便地合成硒代吲哚。
Chem Commun (Camb). 2018 Aug 2;54(63):8781-8784. doi: 10.1039/c8cc04543g.
5
An efficient t-BuOK promoted C3-chalcogenylation of indoles with dichalcogenides.一种高效的 t-BuOK 促进吲哚与二卤代物的 C3-硫代/硒代反应。
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6
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8
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Chemistry. 2018 Mar 15;24(16):4173-4180. doi: 10.1002/chem.201705404. Epub 2018 Jan 25.
9
Regioselective synthesis of 2,3'-biindoles mediated by an NBS-induced homo-coupling of indoles.
Org Biomol Chem. 2017 Nov 22;15(45):9622-9629. doi: 10.1039/c7ob02312j.
10
Selective photocatalysis of lignin-inspired chemicals by integrating hybrid nanocatalysis in microfluidic reactors.在微流控反应器中集成混合纳米催化作用,实现木质素启发型化学品的选择性光催化。
Chem Soc Rev. 2017 Nov 13;46(22):6675-6686. doi: 10.1039/c7cs00257b.