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- W2952330700 abstract "Fluorinated organic compounds are produced in abundance by the pharmaceutical and agrochemical industry, making such compounds attractive as building blocks for further functionalization. Unfortunately, activation of C(sp3)-F bond in saturated fluorocarbons, especially for aliphatic gem-difluoroalkanes, remains challenging. Here we describe the selective activation of inert C(sp3)-F bonds catalyzed by B(C6F5)3. In hexafluoro-2-propanol (HFIP), chemically robust aliphatic gem-difluorides are converted in high yields to the corresponding substituted 2,2',3,3'-tetrahydro-1,1'-spirobiindenes via a B(C6F5)3-catalyzed intramolecular cascade Friedel-Crafts cyclization, not requiring a silicon-based trapping reagent. However, in the absence of a hydrogen-bonding donor solvent such as HFIP, the aliphatic gem-difluorides preferentially engage in a defluorination/elimination process that provides monofluorinated alkenes in good yields. Furthermore, a series of substituted 1-alkyl-2,3-dihydro-1H-indenes was obtained in high yield from the B(C6F5)3-catalyzed defluorinative cyclization of aliphatic secondary monofluorides in HFIP. The protocol could inspire development of a new class of main-group Lewis acid-catalyzed C(sp3)-F bond activation in general unactivated fluorocarbons." @default.
- W2952330700 created "2019-06-27" @default.
- W2952330700 creator A5033082537 @default.
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- W2952330700 date "2019-07-01" @default.
- W2952330700 modified "2023-10-13" @default.
- W2952330700 title "Activation of Saturated Fluorocarbons to Synthesize Spirobiindanes, Monofluoroalkenes, and Indane Derivatives" @default.
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- W2952330700 doi "https://doi.org/10.1016/j.isci.2019.06.018" @default.
- W2952330700 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6612000" @default.
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