32454-33-4

547-63-7

766-85-8

32454-33-4

In a glove box, lithium 2,2,6,6-tetramethylpiperidine (LiTMP, 70.7 mg, 0.48 mmol, 1.2 eq.) was dissolved in toluene (1.5 mL) followed by addition of carbonyl compounds (3, 4.48 mmol, 1.2 eq.). After stirring for 15 minutes at room temperature, a solution of Pd(I) iodide dimer (for aryl iodide: 2.3 mg, 0.004 mmol, 1 mol%; for aryl bromide: 17.4 mg, 0.02 mmol, 5 mol%) and aryl halide (4, X=I or Br, 0.4 mmol, 1.0 eq.) in toluene (0.5 mL) was added. The reaction mixture was continued to be stirred at room temperature for 4-18 hours (reaction progress was monitored by GCMS). Upon completion of the reaction, the crude product was adsorbed directly onto silica (washed with ether) and purified by fast column chromatography.