Halodefluorination of unactivated trifluoromethyl compound and MOFs doped with boronic acid for glucose sensing

Fluorinated organic compounds represent a significant area in modern chemical science, with widespread applications in pharmaceuticals, agrochemicals, and materials due to the unique physicochemical properties conferred by the carbon–fluorine (C–F) bond. Despite their benefits, the exceptional strength and stability of C–F bonds pose substantial synthetic and environmental challenges, particularly in the modification and degradation of C–F containing compounds. Chapter 1 of this thesis provides a detailed review of the roles and applications of fluorinated molecules and discusses current strategies for C–F bond activation, focusing on transition metal catalysis, radical and electrochemical methods, and Lewis acid-mediated pathways. Special attention is given to the emerging utility of main-group Lewis acids—especially those derived from phosphorus, silicon, aluminum, and boron—for the chemoselective cleavage and transformation of benzylic C–F bonds.Building upon this foundational knowledge, Chapter 2 presents an original investigation into the halodefluorination (HDF) of unactivated trifluoromethyl groups, specifically 2,2,2-trifluoroethylbenzene. The research explores the use of iron(III) triflate [Fe(OTf)3] and boron trichloride (BCl3) to selectively replace fluorine atoms with chlorine or bromine. The study evaluates the influence of reaction parameters—including catalyst loading, BCl3 equivalence, and reaction time—on product distribution and yield. Notably, a novel triflate product was isolated and characterized. A detailed plausible mechanistic framework involving a phenonium ion and subsequent nucleophilic substitutions is proposed. The products derived from Chlorodefluorination (CDF), include triflate 36, styrene dichloride 37, and a triple-halex product 38. They possess significant synthetic utility as intermediates in pharmaceutical and materials chemistry.