{"title":"CO2-facilitated radical sequential (3 + 2) annulation of 1,6-enynes via cooperation of sulfinate catalysis and photocatalysis†","authors":"Yuzhen Gao, Siqing Liu and Weiping Su","doi":"10.1039/D3GC02326E","DOIUrl":null,"url":null,"abstract":"<p >Reported here is the CO<small><sub>2</sub></small>-facilitated radical sequential (3 + 2) annulation of 1,6-enynes that proceeds under the concerted catalysis of sulfinate and a photocatalyst (PC) to construct benzo-fused tricyclic scaffolds, that is tetrahydrofluorenes and their N-heterocyclic analogues, in generally good yields. This CO<small><sub>2</sub></small>-facilitated method allows the stable aromatic groups of 1,6-enynes to undergo radical addition-induced dearomatization and rearomatization under metal-, external oxidant- and base-free conditions and features a broad scope of 1,6-enyne substrates, as demonstrated by more than 60 examples including a series of 1,6-enyne derivatives of complex bioactive compounds. Importantly, CO<small><sub>2</sub></small> as a green additive is disclosed to be essential for achieving this reaction with good efficiency, demonstrating a new role of CO<small><sub>2</sub></small> in this transformation.</p>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":" 18","pages":" 7335-7343"},"PeriodicalIF":9.3000,"publicationDate":"2023-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2023/gc/d3gc02326e","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Reported here is the CO2-facilitated radical sequential (3 + 2) annulation of 1,6-enynes that proceeds under the concerted catalysis of sulfinate and a photocatalyst (PC) to construct benzo-fused tricyclic scaffolds, that is tetrahydrofluorenes and their N-heterocyclic analogues, in generally good yields. This CO2-facilitated method allows the stable aromatic groups of 1,6-enynes to undergo radical addition-induced dearomatization and rearomatization under metal-, external oxidant- and base-free conditions and features a broad scope of 1,6-enyne substrates, as demonstrated by more than 60 examples including a series of 1,6-enyne derivatives of complex bioactive compounds. Importantly, CO2 as a green additive is disclosed to be essential for achieving this reaction with good efficiency, demonstrating a new role of CO2 in this transformation.
期刊介绍：
Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.
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