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dc.contributor.authorGhosh, S.-
dc.contributor.authorQu, Z-W.-
dc.contributor.authorRoy, S.-
dc.contributor.authorGrimme, S.-
dc.contributor.authorChatterjee, I.-
dc.date.accessioned2024-10-23T13:17:05Z-
dc.date.available2024-10-23T13:17:05Z-
dc.date.issued2024-10-23-
dc.identifier.urihttp://dspace.iitrpr.ac.in:8080/xmlui/handle/123456789/4754-
dc.description.abstractSelective defluorinative functionalization of trifluoromethyl ketones is a long-standing challenge owing to the exhaustive mode of the process. To meet the demands for the installation of the gem-difluoromethylene unit for the construction of the molecular architectures of well-known pharmaceuticals and agrochemicals, a distinct pathway is thereby highly desirable. Here, a protocol is introduced that allows the divergent synthesis of gem-difluoromethylene group containing tetrahydrofuran derivatives and linear ketones via single C−F bond activation of trifluoromethyl ketones using visible-light photoredox catalysis in the presence of suitable olefins as trapping partner. The choice of appropriate solvent and catalyst plays a significant role in controlling the divergent behavior of this protocol. Highly reducing photo-excited catalysts are found to be responsible for the generation of α,α-difluoromethyl ketone (DFMK) radicals as the key intermediate via a SET process. This protocol also results in a high diastereoselectivity towards the formation of partially fluorinated cyclic ketal derivatives with simultaneous construction of one C−C and two C−O bonds. State-of-the-art DFT calculations are performed to address the origin of diastereoselectivity as well as the divergence of this protocol.en_US
dc.language.isoen_USen_US
dc.subjectcyclic ketalsen_US
dc.subjectC−F bond activationen_US
dc.subjectdensity functional calculationsen_US
dc.subjectfluorinated solventen_US
dc.subjectgem-difluoromethylene uniten_US
dc.subjectphotoredox catalysisen_US
dc.titlePhotoredox Catalyzed Single C−F Bond Activation of Trifluoromethyl Ketones: A Solvent Controlled Divergent Access of gem-Difluoromethylene Containing Scaffoldsen_US
dc.typeArticleen_US
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