A Consecutive Two-Step Radical-Mediated Cyclization of gem-Difluorinated Diynes to Access gem-Difluorinated Cedrenes
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Issued Date
2025-01-01
Resource Type
ISSN
18614728
eISSN
1861471X
Scopus ID
2-s2.0-85218138789
Journal Title
Chemistry - An Asian Journal
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SCOPUS
Bibliographic Citation
Chemistry - An Asian Journal (2025)
Suggested Citation
Thaharn W., Soorukram D., Kuhakarn C. A Consecutive Two-Step Radical-Mediated Cyclization of gem-Difluorinated Diynes to Access gem-Difluorinated Cedrenes. Chemistry - An Asian Journal (2025). doi:10.1002/asia.202401502 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/105453
Title
A Consecutive Two-Step Radical-Mediated Cyclization of gem-Difluorinated Diynes to Access gem-Difluorinated Cedrenes
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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.