A. Kononov , S. Strekalova , E. Kobeleva , G. Savelyev , A. Zlygostev , M. Khvorova , V. Morozov , O. Babaeva , Y. Budnikova
{"title":"芳香族化合物电氧化反应中 C-C 和 C-N 键的形成","authors":"A. Kononov , S. Strekalova , E. Kobeleva , G. Savelyev , A. Zlygostev , M. Khvorova , V. Morozov , O. Babaeva , Y. Budnikova","doi":"10.1016/j.crgsc.2024.100406","DOIUrl":null,"url":null,"abstract":"<div><p>Atom-economical, eco-efficient, metal- and chemical oxidant-free formation of C–C and C–N bond from C(sp<sup>2</sup>)−H and C(sp<sup>3</sup>)−H of arenes toward the direct synthesis of biaryls and anilides or <em>N</em>-benzylamides under mild electro-oxidative conditions is described. The products of C–C and C–N coupling are obtained in up to 88% yields. Aromatic substrates that are oxidized at potentials less positive than +2 V or have bulky bromine or iodine substituents undergo homo-coupling reactions by anodic oxidation to form biaryls or dimers. Aromatic substrates that are difficult to oxidize (<em>E</em><sub>ox</sub> > +2 V) preferentially form anilides and <em>N</em>-benzylamides upon anodic oxidation. The presence of a chlorine substituent on the aromatic ring leads to the formation of both biaryls and anilides during electro-oxidation.</p></div>","PeriodicalId":296,"journal":{"name":"Current Research in Green and Sustainable Chemistry","volume":"8 ","pages":"Article 100406"},"PeriodicalIF":0.0000,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666086524000110/pdfft?md5=8f515219cf599fe9959383ffcc0666d2&pid=1-s2.0-S2666086524000110-main.pdf","citationCount":"0","resultStr":"{\"title\":\"C–C and C–N bond formation in electro-oxidation reactions of aromatic compounds\",\"authors\":\"A. Kononov , S. Strekalova , E. Kobeleva , G. Savelyev , A. Zlygostev , M. Khvorova , V. Morozov , O. Babaeva , Y. Budnikova\",\"doi\":\"10.1016/j.crgsc.2024.100406\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Atom-economical, eco-efficient, metal- and chemical oxidant-free formation of C–C and C–N bond from C(sp<sup>2</sup>)−H and C(sp<sup>3</sup>)−H of arenes toward the direct synthesis of biaryls and anilides or <em>N</em>-benzylamides under mild electro-oxidative conditions is described. The products of C–C and C–N coupling are obtained in up to 88% yields. Aromatic substrates that are oxidized at potentials less positive than +2 V or have bulky bromine or iodine substituents undergo homo-coupling reactions by anodic oxidation to form biaryls or dimers. Aromatic substrates that are difficult to oxidize (<em>E</em><sub>ox</sub> > +2 V) preferentially form anilides and <em>N</em>-benzylamides upon anodic oxidation. The presence of a chlorine substituent on the aromatic ring leads to the formation of both biaryls and anilides during electro-oxidation.</p></div>\",\"PeriodicalId\":296,\"journal\":{\"name\":\"Current Research in Green and Sustainable Chemistry\",\"volume\":\"8 \",\"pages\":\"Article 100406\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.sciencedirect.com/science/article/pii/S2666086524000110/pdfft?md5=8f515219cf599fe9959383ffcc0666d2&pid=1-s2.0-S2666086524000110-main.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Current Research in Green and Sustainable Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666086524000110\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Materials Science\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Research in Green and Sustainable Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666086524000110","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Materials Science","Score":null,"Total":0}
C–C and C–N bond formation in electro-oxidation reactions of aromatic compounds
Atom-economical, eco-efficient, metal- and chemical oxidant-free formation of C–C and C–N bond from C(sp2)−H and C(sp3)−H of arenes toward the direct synthesis of biaryls and anilides or N-benzylamides under mild electro-oxidative conditions is described. The products of C–C and C–N coupling are obtained in up to 88% yields. Aromatic substrates that are oxidized at potentials less positive than +2 V or have bulky bromine or iodine substituents undergo homo-coupling reactions by anodic oxidation to form biaryls or dimers. Aromatic substrates that are difficult to oxidize (Eox > +2 V) preferentially form anilides and N-benzylamides upon anodic oxidation. The presence of a chlorine substituent on the aromatic ring leads to the formation of both biaryls and anilides during electro-oxidation.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
