Evaluation of effects of various solvents and additives on the regioselectivity. (A) Effects of solvents on benzylic C–N cross coupling reaction. (B) Regioselectivity switch observed in cross coupling of 1a and 2a with different additives. Conditions identical to those shown in part A, using 10 mol% additive instead of TBABr, 10 mol % CuBr2 instead of CuCl, and DCM:HFIP (7:3) solvent. a Monitored by 1H NMR spectroscopy, yield determined using 0.2 mmol mesitylene as internal standard. TBA, tetrabutylammonium; DCM, dichloromethane; HFIP, hexafluoroisopropanol. b Reaction run with TBA+Cl− instead of TBABr. c Reaction run at 60 °C.