N-Methyl-N-[(trifluoromethyl)thio]-p-toluenesulfonamide

Experimental procedure²⁾: To a flask are added the boronic acid (0.50 mmol, 1.0 eq.), 4,4'-dimethyl-2,2'-bipyridyl (0.10 mmol, 20 mol%), CuI (0.05 mmol, 10 mol%), diglyme (1.5 mL), N-methyl-N-[(trifluoromethyl)thio]-p-toluenesulfonamide (0.60 mmol, 1.2 eq.) and finally distilled water (3.50 mmol, 7.0 eq.). The reaction mixture is stirred for 15 h at room temperature. The reaction is partitioned between pentane and water. The aqueous layer is extracted with pentane and the combined organic layers are washed with brine, dried over Na₂SO₄, filtered and concentrated to dryness. The crude residue is purified by flash chromatography to afford the desired product.