Hazuki Miyake, Nico Ishige, Hayaki Okai and Hiroki Iida
{"title":"Aerobic oxidative C–C bond formation through C–H bond activation catalysed by flavin and iodine†","authors":"Hazuki Miyake, Nico Ishige, Hayaki Okai and Hiroki Iida","doi":"10.1039/D4OB01317D","DOIUrl":null,"url":null,"abstract":"<p >We report a metal/light-free aerobic oxidative C–C bond formation using sp<small><sup>3</sup></small> C–H bond activation of tetrahydroisoquinolines catalyzed by flavin and iodine. The dual catalytic system enabled the oxidative Mannich and aza-Henry reactions by the cross-dehydrogenative coupling between two sp<small><sup>3</sup></small> C–H bonds. Furthermore, the flavin–iodine-coupled catalysis was applied to the synthesis of pyrrolo[2,1-<em>a</em>]isoquinolines through the sequential oxidative 1,3-dipolar cycloaddition and dehydrogenative aromatization. The biomimetic flavin catalysis efficiently activates molecular oxygen; thus the non-metal dual catalytic system enables green oxidative transformation using molecular oxygen as an environmentally friendly terminal oxidant which generates benign water.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/ob/d4ob01317d","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We report a metal/light-free aerobic oxidative C–C bond formation using sp3 C–H bond activation of tetrahydroisoquinolines catalyzed by flavin and iodine. The dual catalytic system enabled the oxidative Mannich and aza-Henry reactions by the cross-dehydrogenative coupling between two sp3 C–H bonds. Furthermore, the flavin–iodine-coupled catalysis was applied to the synthesis of pyrrolo[2,1-a]isoquinolines through the sequential oxidative 1,3-dipolar cycloaddition and dehydrogenative aromatization. The biomimetic flavin catalysis efficiently activates molecular oxygen; thus the non-metal dual catalytic system enables green oxidative transformation using molecular oxygen as an environmentally friendly terminal oxidant which generates benign water.