{"title":"咪唑[1,5- A]吡啶的C - h功能化:亚甲基插入进入C(sp2) -C (sp3) -H-C (sp2)键形成的无金属途径","authors":"Shivangani Mahajan, and , Sanghapal D. Sawant*, ","doi":"10.1021/acsomega.4c0382310.1021/acsomega.4c03823","DOIUrl":null,"url":null,"abstract":"<p >Formaldehyde has been used as a solvent and a source of carbon to insert a methylene group for bridging two imidazo[1,5-<i>a</i>]pyridine molecules without using any metal catalysis. This strategy has been extended on other alkyl-, aryl-, and heteroaryl aldehydes as well. This C(sp<sup>2</sup>)–C(sp<sup>3</sup>)–H–C(sp<sup>2</sup>) bond forming reaction proceeds via C(sp<sup>2</sup>)H functionalization of imidazo[1,5-<i>a</i>]pyridine and was applied on a wide range of substrates offering moderate to good yields of methylene-bridged/inserted bis-imidazo[1,5-<i>a</i>]pyridines. Most importantly, as an application, the bis-heteroarene product has been demonstrated as a ligand. The ligand-like behavior of bis-imidazo[1,5-<i>a</i>]pyridines has been demonstrated as an extension of current methodology. This reaction works well at the gram scale level.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":"9 50","pages":"49071–49080 49071–49080"},"PeriodicalIF":3.7000,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c03823","citationCount":"0","resultStr":"{\"title\":\"C–H Functionalization of Imidazo[1,5-a]pyridines: A Metal-Free Approach for Methylene Insertion to Access C(sp2)–C(sp3)–H–C(sp2) Bond Formation\",\"authors\":\"Shivangani Mahajan, and , Sanghapal D. Sawant*, \",\"doi\":\"10.1021/acsomega.4c0382310.1021/acsomega.4c03823\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Formaldehyde has been used as a solvent and a source of carbon to insert a methylene group for bridging two imidazo[1,5-<i>a</i>]pyridine molecules without using any metal catalysis. This strategy has been extended on other alkyl-, aryl-, and heteroaryl aldehydes as well. This C(sp<sup>2</sup>)–C(sp<sup>3</sup>)–H–C(sp<sup>2</sup>) bond forming reaction proceeds via C(sp<sup>2</sup>)H functionalization of imidazo[1,5-<i>a</i>]pyridine and was applied on a wide range of substrates offering moderate to good yields of methylene-bridged/inserted bis-imidazo[1,5-<i>a</i>]pyridines. Most importantly, as an application, the bis-heteroarene product has been demonstrated as a ligand. The ligand-like behavior of bis-imidazo[1,5-<i>a</i>]pyridines has been demonstrated as an extension of current methodology. This reaction works well at the gram scale level.</p>\",\"PeriodicalId\":22,\"journal\":{\"name\":\"ACS Omega\",\"volume\":\"9 50\",\"pages\":\"49071–49080 49071–49080\"},\"PeriodicalIF\":3.7000,\"publicationDate\":\"2024-12-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c03823\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Omega\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acsomega.4c03823\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Omega","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsomega.4c03823","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
C–H Functionalization of Imidazo[1,5-a]pyridines: A Metal-Free Approach for Methylene Insertion to Access C(sp2)–C(sp3)–H–C(sp2) Bond Formation
Formaldehyde has been used as a solvent and a source of carbon to insert a methylene group for bridging two imidazo[1,5-a]pyridine molecules without using any metal catalysis. This strategy has been extended on other alkyl-, aryl-, and heteroaryl aldehydes as well. This C(sp2)–C(sp3)–H–C(sp2) bond forming reaction proceeds via C(sp2)H functionalization of imidazo[1,5-a]pyridine and was applied on a wide range of substrates offering moderate to good yields of methylene-bridged/inserted bis-imidazo[1,5-a]pyridines. Most importantly, as an application, the bis-heteroarene product has been demonstrated as a ligand. The ligand-like behavior of bis-imidazo[1,5-a]pyridines has been demonstrated as an extension of current methodology. This reaction works well at the gram scale level.
ACS OmegaChemical Engineering-General Chemical Engineering
CiteScore
6.60
自引率
4.90%
发文量
3945
审稿时长
2.4 months
期刊介绍:
ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.