与自由基催化有关的噻唑-2-吡啶二聚体的氧化还原性质研究

IF 3.3 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Organic & Inorganic Au Pub Date : 2023-03-27 DOI:10.1021/acsorginorgau.3c00008

Ludivine Delfau, Nadhrata Assani, Samantha Nichilo, Jacques Pecaut, Christian Philouze, Julie Broggi, David Martin* and Eder Tomás-Mendivil*,

{"title":"与自由基催化有关的噻唑-2-吡啶二聚体的氧化还原性质研究","authors":"Ludivine Delfau, Nadhrata Assani, Samantha Nichilo, Jacques Pecaut, Christian Philouze, Julie Broggi, David Martin* and Eder Tomás-Mendivil*, ","doi":"10.1021/acsorginorgau.3c00008","DOIUrl":null,"url":null,"abstract":"We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (Eox = −0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied in the literature. In addition, a remarkable potential gap between the first and second oxidation of the dimer also allows for the isolation of the corresponding air-persistent radical cation. The latter is an unexpected efficient promoter of the radical transformation of α-bromoamides into oxindoles.","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2023-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/89/cf/gg3c00008.PMC10251502.pdf","citationCount":"0","resultStr":"{\"title\":\"On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis\",\"authors\":\"Ludivine Delfau, Nadhrata Assani, Samantha Nichilo, Jacques Pecaut, Christian Philouze, Julie Broggi, David Martin* and Eder Tomás-Mendivil*, \",\"doi\":\"10.1021/acsorginorgau.3c00008\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (Eox = −0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied in the literature. In addition, a remarkable potential gap between the first and second oxidation of the dimer also allows for the isolation of the corresponding air-persistent radical cation. The latter is an unexpected efficient promoter of the radical transformation of α-bromoamides into oxindoles.\",\"PeriodicalId\":29797,\"journal\":{\"name\":\"ACS Organic & Inorganic Au\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2023-03-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/89/cf/gg3c00008.PMC10251502.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Organic & Inorganic Au\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acsorginorgau.3c00008\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Organic & Inorganic Au","FirstCategoryId":"1085","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsorginorgau.3c00008","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

我们报道了从流行的噻唑-2-亚基有机催化剂中分离和研究二聚体。以2,6-二（异丙基）苯基（Dip）N-取代基为特征的模型被发现是比文献中先前研究的双（噻唑-2-亚基）更强的还原剂（Eox=−0.8 V vs SCE）。此外，二聚体的第一次和第二次氧化之间的显著电势差也允许分离相应的空气持久性自由基阳离子。后者是α-溴酰胺自由基转化为羟吲哚的出乎意料的有效促进剂。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis

查看原文本刊更多论文

On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis

We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (E_ox = −0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied in the literature. In addition, a remarkable potential gap between the first and second oxidation of the dimer also allows for the isolation of the corresponding air-persistent radical cation. The latter is an unexpected efficient promoter of the radical transformation of α-bromoamides into oxindoles.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

ACS Organic & Inorganic Au 有机化学、无机化学-

CiteScore

4.10

自引率

0.00%

发文量

期刊介绍： ACS Organic & Inorganic Au is an open access journal that publishes original experimental and theoretical/computational studies on organic organometallic inorganic crystal growth and engineering and organic process chemistry. Short letters comprehensive articles reviews and perspectives are welcome on topics that include:Organic chemistry Organometallic chemistry Inorganic Chemistry and Organic Process Chemistry.