Activation of Saturated Fluorocarbons to Synthesize Spirobiindanes, Monofluoroalkenes, and Indane Derivatives.

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 re

SUBMITTER: Wang J 

PROVIDER: S-EPMC6612000 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature