Iodine mediated synthesis of diaryl diselenides using SeO<sub>2</sub> as a selenium source

Dileep, Kommula; Li, Qing; Ning, Siyang; Liu, Wujun; Wang, Qian; Zhao, Zongbao K.

doi:10.1080/00397911.2020.1728775

Cited by 13 publications

(7 citation statements)

References 43 publications

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“…The synthesis of the unsaturated carboxylic acids and 2r were carried out using known literature procedures. ,,− 2a–q were commercially accessible.…”

Section: Methodsmentioning

confidence: 99%

Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

et al. 2021

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An efficient aerobic iron-catalyzed annulation of unsaturated carboxylic acids with disulfides has been developed. This procedure proceeds using FeCl 3 as the catalyst and KI as an iodine source under an air atmosphere, which provides practical access to a wide range of substituted γ-lactone derivatives. The disclosed method is quite simple, highly atom-economic, environmentally friendly, and tolerates a broad substrate scope.

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“…The synthesis of the unsaturated carboxylic acids and 2r were carried out using known literature procedures. ,,− 2a–q were commercially accessible.…”

Section: Methodsmentioning

confidence: 99%

Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

et al. 2021

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“…[1e] The increasing demand for diselenides has prompted the development of their synthetic methods. Various selenium reagents such as selenocyanates, [45] selenols, [46] SeO 2 , [47] Na 2 Se 2 , [48] SmSe 2 [49] and (EtO) 2 P(O)SeNa [50] have been employed to construct diselenides.…”

Section: The Synthesis Of Diselenides With Elemental Seleniummentioning

confidence: 99%

Synthesis of Organoselenium Compounds with Elemental Selenium

Liu

Zhou

et al. 2021

Adv Synth Catal

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In the recent decade, growing efforts have been devoted to employing elemental selenium as a selenium source in organic synthesis. In contrast to unstable, smelly, and toxic previous selenium reagents, elemental selenium is readily available, cheap, bench-stable, and easy to handle. This review will mainly focus on the strategies for the activation of elemental selenium and the synthesis of organoselenium compounds including monoselenides, diselenides, selenium-containing heterocycles and so on. The Synthesis ofMonoselenides with Elemental Selenium 2.2. The Synthesis of Diselenides with Elemental Selenium 2.3. The Synthesis of Selenium-Containing Heterocycles with Elemental Selenium 2.4. The Synthesis of Other Organoselenium Compounds with Elemental Selenium 3. Conclusions

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“…所有反应在 Schlenk 管中氮气氛围下进行, 实验常用溶剂和催化剂 ICl 均从北京伊诺凯有限公司购买, 并直接使用. 原料 4-苯氨基香豆素 [37] 和二芳(烷)基二硒醚 [38] 通过文献方法制备.…”

Section: 仪器与试剂unclassified

ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives

He¹,

Zhang²,

Wu³

et al. 2021

Chinese Journal of Organic Chemistry

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Owing to their special biological activities, organic selenium heterocyclic compounds have widely applications in organic chemistry and drug synthesis. A series of methods for the synthesis of organoselenide heterocyclic compounds have been reported, however, shortcomings still exist. In this paper, an effective method for the synthesis of 3-aryl(alkyl)selenylcoumarin derivatives via the ICl-catalyzed selenation of coumarins with diaryl(alkyl)diselenide at room temperature is reported. In addition, this method is also suitable for the construction of Csp2-Se bonds of other heterocyclic compounds. Compared to previous methods, this method has the advantages of mild conditions and wide functional groups tolerance, providing a general pathway to organoselenide heterocyclic compounds. Keywords Iodine cation-catalyzed selenation; Construction of Csp2-Se; Heterocyclic compounds; Diaryl(alkyl)diselenides 香豆素衍生物具有良好的生物活性, 成为抗肿瘤药物研发的研究热点 [1][2][3][4] . 与其他抗肿瘤活性药物相比, 香豆素衍生物具有药理运用广泛、分子量小、合成简便和毒性弱等特点 [5][6][7] . 在农业生产方面, 香豆素衍生物可以作为杀虫剂和植物保护素 [8][9][10] . 此外, 香豆素衍生物作为荧光探针, 可以应用于水体中污染物分析 [11][12][13] . 同时, 香豆素类化合物还可以应用于制作荧光增白剂、荧光指示剂以及荧光染料 [14][15][16] . 由于香豆素衍生物在很多领域具有重要的应用, 众多关于香豆素及其衍生物合成的方法被相继报道 [17][18][19][20] .有机硒化合物因其良好的生物学活性, 在医药和有机合成中具有广泛的应用, 特别是在抗癌、心血管保护、抗病毒、免疫调节及神经保护等方面均具有重要应用 [21][22][23][24] . 硒原子可以作为电子供体或氢键受体, 以修饰酶活性位点的化学特征, 因此硒化的杂环化合物具有独特的生物学活性与化学性质 [25] . 目前, 关于香豆素衍生物 C sp 2-Se 键构建方法主要有以下几种: 卤代烃脱卤芳硒化反应是构建 C-Se 键的重要方法, 但该方法至少需要等物质的量的卤素作为预卤化试剂, 不符合原子经济性要求 [26] . 杂环化合物 C-H 交叉脱氢氧化偶联(CDC) 反应在一定程度上解决了预官能团化问题, 且具有很好的原子经济性. 最近, 曲阜师范大学魏伟课题组报道了 (NH 4 ) 2 S 2 O 8 存在下, 可见光诱导 4-苯胺香豆素和二芳基二硒化物 C-H 交叉脱氢氧化偶联反应制备有机硒香豆

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Iodine mediated synthesis of diaryl diselenides using SeO₂ as a selenium source

Cited by 13 publications

References 43 publications

Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

Synthesis of Organoselenium Compounds with Elemental Selenium

ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives

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Iodine mediated synthesis of diaryl diselenides using SeO2 as a selenium source

Cited by 13 publications

References 43 publications

Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

Synthesis of Organoselenium Compounds with Elemental Selenium

ICl-Catalyzed Csp2—H Selenation of Aminocoumarin Derivatives

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Product

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Iodine mediated synthesis of diaryl diselenides using SeO₂ as a selenium source

ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives