Hydrofluorocarbons (HFCs) are widely used as cooling agents in refrigerators and air conditioners and as solvents in industrial processes. However, their application has been restricted by their high global warming potential. Thus, strategies for HFC decomposition and effective utilization are urgently required. Herein, we describe a method for the chemical transformation of two HFCs, viz. HFC-23 and HFC-125, based on the continuous-flow perfluoroalkylation of esters to synthesize the pharmaceutically and agrochemically vital trifluoromethyl and pentafluoroethyl ketones. The combination of a potassium base and a glyme solvent system is found to be the most effective. The proposed method is attractive for industrial use because it allows the consumption of a large volume of HFCs, promotes the synthesis of high-value medicinal compounds, and serves as an ideal alternative to the current HFC decomposition processes like thermal plasma treatment.
A protocol for the stereodivergent pentafluoroethylation
of N-sulfinylimines using HFC-125 with KHMDS/triglyme
has been
developed. Both diastereomers of the pentafluoroethylated amines can
be selectively synthesized based on the presence or absence of triglyme.
This additive-controlled protocol allows the KHMDS/triglyme cryptate
to be a straightforward and cheap alternative to previously reported
base-controlled stereodivergent trifluoromethylation using potassium
hexamethyldisilazide (KHMDS) versus P4-
t
Bu.
Pyridine-tetrafluoro-λ6-sulfanyl-alkynes have emerged as building blocks for synthesizing linearly-linked pyridine-heterocycles. They are prepared via a two-step procedure comprising the radical addition of pyridine-tetrafluoro-λ6-sulfanyl-chlorides and alkynes and subsequent base-promoted elimination of HCl. Herein we developed a straightforward alternative synthesis via the radical coupling of pyridine-tetrafluoro-λ6-sulfanyl-chlorides with ethynylbenziodoxolone reagents under LED irradiation.
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