Potassium [[(tert-Butoxycarbonyl)amino]methyl]trifluoroborate

General Procedure for the Suzuki?Miyaura Cross-coupling Reaction: A sealed tube is charged with potassium (tert-butoxycarbonyl)amino)methyl)trifluoroborate (62 mg, 0.263 mmol, 1.05 equiv), an aryl or heteroaryl chloride (0.25 mmol, 1.0 equiv), Pd(OAc)₂ (3 mg, 0.013 mmol, 0.05 equiv), SPhos ligand (0.03 mmol, 0.1 equiv) and K₂CO₃ (104 mg, 0.75 mmol, 3.0 equiv). The mixture is then purged with argon. Toluene/H₂O (4:1, 0.8 mL / 0.2 mL) is then added to the reaction tube. The reaction mixture is stirred for 22 h at 85 °C and then cooled to rt. A solution of pH 7 buffer (2 mL) is added, and the resulting mixture is extracted with EtOAc (2 × 3 mL). The organic layer is combined, dried (MgSO₄) and filtered. The solvent is removed in vacuo and the product is purified by column chromatography to give the corresponding compound in shown yield.