In nature, enzymes such as cytochrome P-450 (Fig. ) demonstrate remarkable efficiency in catalyzing stereoselective oxidations , utilizing an iron-porphyrin center to target C(sp 3 )-H bonds . Inspired by the high oxidation state (Fe(IV)) iron-oxo complexes in heme-containing enzymes, we hypothesized that increasing the electropositivity at the metal center of catalysts may benefit the enantioselective oxidation of the C(sp 3 )-H bonds (Fig. ) . Our strategy employs a bulky counter anion, tetrakis phenyl]borate (BArF‾), to enhance the electropositivity of the copper center of the catalyst (Fig. ). This electropositivity enhancement improves the coordination of carboxylic acids with copper, and facilitates their interactions with radicals generated by the C(sp 3 )-H hydrogen atom abstraction. Crucially, the anion BArF‾ stabilizes the copper III intermediate, which undergoes reductive elimination to form the C-O bond.