Moving the trifluoromethyl group to the ortho position (reagent 35B, entry 8) led to a slight improvement. The addition of another CF3 group (reagent 16, entry 9) had a profound effect delivering 27 as the major product (53% yield) with only a small amount of 26 (5%) being observed. Increasing the Co-loading (entry 10) led to increased olefin isomerization (24) while altering the Co-source dramatically reduced the yield (entries 11-12). An exploration of silanes (entries 13-15) confirmed that PhSiMeH2 was ideally suited for the reaction. The final optimized conditions are simple to perform: A flask containing olefin (1.0 equiv.), Co II (salen)-I (0.7 mol%), and nitroamide 16 (1.3 equiv.) is purged with Ar followed by addition of i-PrOH (0.13 M), silane (1.3 equiv.), and TBHP (1.0 equiv.). After stirring at room temperature for 9 hours the reaction is quenched (sat. aq. NH4Cl), extracted (DCM), and purified. Although dry i-PrOH is employed, strictly anhydrous conditions are not required (the deliberate addition of 55 equiv. of water leads to ca. 8% lower yield, see SI).