Abstract
The active geminal chloro‑copper (CF3CFClCu) and vinyl copper (CF3CF=CCuCF3) intermediates produced good results (> 70%) in preparing F-epoxides and F-enones, respectively. The elimination of copper chloride as the driving force in F-epoxide formation occurred intra-molecularly and intermolecularly in F-enones. The copper intermediates were prepared in situ from the corresponding silver precursors via a Ag-Cu exchange reaction. The subsequent epoxide ring-opening with metal fluorides gave ketones in > 80% yields, showing that this approach can produce other functionalized fluorocarbons. Stable CF3CF2Cu yielded 30% of ketones when reacted with fluorinated acid chlorides. The geminal chlorine atom makes a big difference in stability and performance between CF3CF2Cu (stable, low yield in ketones) and CF3CFClCu (unstable, the higher output of epoxides).
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