Suppr超能文献

无金属 - 5-巯基四唑和 2-巯基吡啶与不对称二芳基碘鎓盐的芳基化反应。

Metal-free -arylation of 5-mercaptotetrazoles and 2-mercaptopyridine with unsymmetrical diaryliodonium salts.

机构信息

Department of Chemical Sciences, Tezpur University, Napaam-784028, Assam, India.

Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati-781039, India.

出版信息

Org Biomol Chem. 2022 May 18;20(19):3890-3896. doi: 10.1039/d2ob00406b.

Abstract

Herein, we demonstrate the application of unsymmetrical iodonium salts towards -arylation of heterocyclic thiols (especially tetrazole-5-thiols and pyridine-2-thiol) under metal-free conditions, affording a diverse range of di(hetero)aryl thioethers in moderate to good yields. A detailed study on the effects of counter-anions and the auxiliary of iodonium salts was conducted. Suitable auxiliary selection of the unsymmetrical iodonium salt offers flexibility for a wide range of aryl moieties and its incorporation into -arylation. The DFT study supports the experimental observations of chemoselective arylation.

摘要

在此,我们展示了不对称碘𬭩盐在无金属条件下用于杂环硫醇(特别是四唑-5-硫醇和吡啶-2-硫醇)的 -芳基化反应,以中等至良好的收率得到了各种不同的二(杂)芳基硫醚。我们详细研究了抗衡阴离子和碘𬭩盐助剂的影响。不对称碘𬭩盐的合适助剂选择为广泛的芳基部分及其 -芳基化提供了灵活性。DFT 研究支持了化学选择性芳基化的实验观察。

相似文献

2
Unsymmetrical Aryl(2,4,6-trimethoxyphenyl)iodonium Salts: One-Pot Synthesis, Scope, Stability, and Synthetic Studies.
J Org Chem. 2016 Mar 4;81(5):1998-2009. doi: 10.1021/acs.joc.5b02833. Epub 2016 Feb 12.
3
An Admix Approach To Determine Counter Anion Effects on Metal-Free Arylation Reactions with Diaryliodonium Salts.
J Org Chem. 2017 Nov 17;82(22):11765-11771. doi: 10.1021/acs.joc.7b01599. Epub 2017 Aug 24.
4
One-pot synthesis of aryl sulfones from organometallic reagents and iodonium salts.
J Org Chem. 2015 Mar 6;80(5):2582-600. doi: 10.1021/jo5027518. Epub 2015 Feb 17.
5
Metal-Free Regioselective N-Arylation of 1-Tetrazoles with Diaryliodonium Salts.
J Org Chem. 2022 Aug 5;87(15):9782-9796. doi: 10.1021/acs.joc.2c00848. Epub 2022 Jul 18.
7
A Metal-free Approach to 3-Aryl-3-hydroxy-2-oxindoles by Treatment of 3-Acyloxy-2-oxindoles with Diaryliodonium Salts.
Chem Asian J. 2016 Jan;11(2):226-30. doi: 10.1002/asia.201500854. Epub 2015 Nov 3.
8
Arylation with unsymmetrical diaryliodonium salts: a chemoselectivity study.
Chemistry. 2013 Jul 29;19(31):10334-42. doi: 10.1002/chem.201300860. Epub 2013 Jun 20.
9
Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts.
Org Lett. 2011 Jul 1;13(13):3462-5. doi: 10.1021/ol2012082. Epub 2011 May 26.
10
Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand.
Angew Chem Int Ed Engl. 2022 Jul 11;61(28):e202201240. doi: 10.1002/anie.202201240. Epub 2022 May 17.

引用本文的文献

1
Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.
Chem Rev. 2025 Mar 26;125(6):3440-3550. doi: 10.1021/acs.chemrev.4c00808. Epub 2025 Mar 7.
3
Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts.
Beilstein J Org Chem. 2024 Nov 13;20:2891-2920. doi: 10.3762/bjoc.20.243. eCollection 2024.
4
Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions.
Beilstein J Org Chem. 2024 May 3;20:1020-1028. doi: 10.3762/bjoc.20.90. eCollection 2024.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验