{"title":"A Consecutive Two-Step Radical-Mediated Cyclization of gem-Difluorinated Diynes to Access gem-Difluorinated Cedrene.","authors":"Watcharaporn Thaharn, Darunee Soorukram, Chutima Kuhakarn","doi":"10.1002/asia.202401502","DOIUrl":null,"url":null,"abstract":"<p><p>A consecutive two-step radical-mediated cyclization of gem-difluoromethylenated bis(3-arylpropagyl)-indane-1,3-diones to access structurally unique gem-difluoromethylenated cedrenes is described. Substituents located on the aryl rings of the two propagyl units play an important role in governing the consecutive cyclization pattern. Upon treatment of gem-difluoromethylenated 1,3-diane with Bu3SnH/AIBN, a tributylstannyl radical-mediated radical cyclization between the two diyne units chemoselectively took place, leading to the corresponding gem-difluoromethylenated acoradienes in good yields, after removal of tributylstannyl group by TFA. Subsequently, Bu3SnH/AIBN promoted reductive cleavage of the phenylsulfanyl group leading to difluoroalkyl radicals which spontaneously underwent radical cyclization to give a series of gem-difluoromethylenated cedrenes.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202401502"},"PeriodicalIF":3.5000,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202401502","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A consecutive two-step radical-mediated cyclization of gem-difluoromethylenated bis(3-arylpropagyl)-indane-1,3-diones to access structurally unique gem-difluoromethylenated cedrenes is described. Substituents located on the aryl rings of the two propagyl units play an important role in governing the consecutive cyclization pattern. Upon treatment of gem-difluoromethylenated 1,3-diane with Bu3SnH/AIBN, a tributylstannyl radical-mediated radical cyclization between the two diyne units chemoselectively took place, leading to the corresponding gem-difluoromethylenated acoradienes in good yields, after removal of tributylstannyl group by TFA. Subsequently, Bu3SnH/AIBN promoted reductive cleavage of the phenylsulfanyl group leading to difluoroalkyl radicals which spontaneously underwent radical cyclization to give a series of gem-difluoromethylenated cedrenes.
期刊介绍：
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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