Cobalt catalysts with electronically enhanced site selectivity have been developed, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp(2))-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl 4-Me-((PNP)-P-iPr)Co(H)(2)BPin (1) and the air-stable cobalt(II) bis(pivalate) 4-Me-((PNP)-P-iPr)Co((O2CBu)-Bu-t)(2) (2) compounds were effective and exhibited broad functional group tolerance across a wide range of fluoroarenes containing electronically diverse functional groups, regardless of the substitution pattern on the arene. The electronically enhanced ortho-to-fluorine selectivity observed with the cobalt catalysts was maintained in the presence of a benzylic dimethylamine and hydrosilanes, overriding the established directing-group effects observed with precious-metal catalysts. The synthetically useful selectivity observed with cobalt was applied to an efficient synthesis of the anti-inflammatory drug flurbiprofen.