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一种在无催化剂和无氧化剂条件下用于富电子芳烃的低成本电化学硫氰化和硒氰化策略。

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions.

作者信息

Zhang Xing, Wang Chenguang, Jiang Hong, Sun Linhao

机构信息

Department of Chemistry, College of Science, Huazhong Agricultural University Wuhan 430070 P. R. China

出版信息

RSC Adv. 2018 Jun 14;8(39):22042-22045. doi: 10.1039/c8ra04407d. eCollection 2018 Jun 13.

DOI:10.1039/c8ra04407d
PMID:35541747
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9081088/
Abstract

A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell. This strategy is versatile for various (hetero)aromatic compounds such as indole, pyrrole, aniline and anisole under mild conditions without any catalyst or oxidant. Readily available salts NHSCN and KSeCN are employed respectively as the sole reagent.

摘要

在恒流电解条件下的无隔膜电解池中,已开发出一种用于富电子芳烃的低成本高效硫氰化和硒氰化策略。该策略在温和条件下,无需任何催化剂或氧化剂,对各种(杂)芳族化合物,如吲哚、吡咯、苯胺和苯甲醚都具有通用性。分别使用易于获得的盐NHSCN和KSeCN作为唯一试剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/249f3fed4437/c8ra04407d-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/4ec3934478d4/c8ra04407d-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/af54af0107af/c8ra04407d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/5a3d52ae837f/c8ra04407d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/249f3fed4437/c8ra04407d-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/4ec3934478d4/c8ra04407d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/4e8d285613dc/c8ra04407d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/692327b48db2/c8ra04407d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/af54af0107af/c8ra04407d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/5a3d52ae837f/c8ra04407d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/88eb/9081088/249f3fed4437/c8ra04407d-s5.jpg

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1
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2
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J Org Chem. 2017 Sep 15;82(18):9312-9320. doi: 10.1021/acs.joc.7b01122. Epub 2017 Aug 30.
3
Electrocatalytic Oxidant-Free Dehydrogenative C-H/S-H Cross-Coupling.
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RSC Adv. 2021 Jun 24;11(36):22305-22316. doi: 10.1039/d1ra01035b. eCollection 2021 Jun 21.
4
Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation.光化学和电化学诱导硫氰化反应的最新进展:一种更绿色的含硫氰基化合物形成方法。
RSC Adv. 2022 Feb 22;12(10):6214-6233. doi: 10.1039/d1ra09060g. eCollection 2022 Feb 16.
5
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Molecules. 2022 Jan 25;27(3):772. doi: 10.3390/molecules27030772.
6
Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds.电氧化是一种很有前途的方法,可以对吡唑类化合物进行功能化。
Molecules. 2021 Aug 5;26(16):4749. doi: 10.3390/molecules26164749.
7
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Chemistry. 2016 Jan 11;22(2):511-6. doi: 10.1002/chem.201504179. Epub 2015 Dec 3.
5
Catalyst-Free Regioselective C-3 Thiocyanation of Imidazopyridines.咪唑并吡啶的无催化剂区域选择性C-3硫氰化反应
J Org Chem. 2015 Nov 6;80(21):11073-9. doi: 10.1021/acs.joc.5b01637. Epub 2015 Oct 8.
6
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J Org Chem. 2015 Aug 21;80(16):8275-81. doi: 10.1021/acs.joc.5b01369. Epub 2015 Aug 5.
7
A visible-light-promoted aerobic metal-free C-3 thiocyanation of indoles.可见光促进的吲哚无金属C-3硫氰化反应。
J Org Chem. 2014 Nov 7;79(21):10588-92. doi: 10.1021/jo5015799. Epub 2014 Oct 21.
8
Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities.含吲哚结构的苯并咪唑氨基甲酸酯的合成与抗肿瘤和抗微管蛋白活性评价。
Eur J Med Chem. 2014 Nov 24;87:306-15. doi: 10.1016/j.ejmech.2014.09.071. Epub 2014 Sep 28.
9
Design, synthesis, and evaluation of multitarget-directed selenium-containing clioquinol derivatives for the treatment of Alzheimer's disease.设计、合成及评价含硒氯碘羟喹啉衍生物作为多靶点药物用于治疗阿尔茨海默病。
ACS Chem Neurosci. 2014 Oct 15;5(10):952-62. doi: 10.1021/cn500119g. Epub 2014 Aug 22.
10
Redox catalysis in organic electrosynthesis: basic principles and recent developments.有机电化学合成中的氧化还原催化:基本原理和最新进展。
Chem Soc Rev. 2014 Apr 21;43(8):2492-521. doi: 10.1039/c3cs60464k. Epub 2014 Feb 5.