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铜催化4-硝基吡唑及其他杂环与硒粉和芳基碘化物的直接C-H芳基硒化反应。不对称杂芳基硒醚的合成方法。

Copper-catalyzed direct C-H arylselenation of 4-nitro-pyrazoles and other heterocycles with selenium powder and aryl iodides. Access to unsymmetrical heteroaryl selenides.

作者信息

Jakubczyk Michał, Mkrtchyan Satenik, Madura Izabela D, Marek Paulina H, Iaroshenko Viktor O

机构信息

Laboratory of Homogeneous Catalysis and Molecular Design at the Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences Sienkiewicza 112 PL-90-363 Łodź Poland

Department of Inorganic Chemistry, Faculty of Chemistry, Warsaw University of Technology Noakowskiego 3 00-664 Warsaw Poland.

出版信息

RSC Adv. 2019 Aug 13;9(44):25368-25376. doi: 10.1039/c9ra05004c.

DOI:10.1039/c9ra05004c
PMID:35530113
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9070035/
Abstract

A one-pot, Cu-catalyzed direct C-H arylselenation protocol using elemental Se and aryl iodides was developed for nitro-substituted, -alkylated pyrazoles, imidazoles and other heterocycles including 4-chromen-4-one. This general and concise method allows one to obtain a large number of unsymmetrical heteroaryl selenides bearing a variety of substituents. The presence of the nitro group was confirmed to be essential for the C-H activation and can also be used for further functionalisation and manipulation. Several examples of heteroannulated benzoselenazines were also synthesized using the developed synthetic protocol.

摘要

开发了一种一锅法、铜催化的直接C-H芳基硒化反应方案,该方案使用元素硒和芳基碘化物,用于硝基取代、烷基化的吡唑、咪唑以及包括4-色满-4-酮在内的其他杂环化合物。这种通用且简洁的方法能够制备大量带有各种取代基的不对称杂芳基硒化物。硝基的存在被证实对于C-H活化至关重要,并且还可用于进一步的官能化和操作。使用所开发的合成方案还合成了几个杂环稠合苯并硒嗪的实例。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/33a596bb6b0e/c9ra05004c-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/7fc0b81cec2e/c9ra05004c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/edf869997ce7/c9ra05004c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/80ab68b13fea/c9ra05004c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/091cf5ae15ff/c9ra05004c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/0bc63e3aac2e/c9ra05004c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/33a596bb6b0e/c9ra05004c-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/7fc0b81cec2e/c9ra05004c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/edf869997ce7/c9ra05004c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/80ab68b13fea/c9ra05004c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/091cf5ae15ff/c9ra05004c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/0bc63e3aac2e/c9ra05004c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ee4/9070035/33a596bb6b0e/c9ra05004c-f5.jpg

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3
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Nanoscale Adv. 2022 Apr 7;4(9):2208-2223. doi: 10.1039/d1na00822f. eCollection 2022 May 3.
4
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硒化物和二硒化物:抗癌和化学预防活性的综述。
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10
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J Org Chem. 2016 Jun 3;81(11):4485-93. doi: 10.1021/acs.joc.6b00229. Epub 2016 May 24.