Sodium Carbonate → HCID 18759616, compound

Participants

Reaction Conditions

Reaction Steps

4-{3-[diallyl(methyl)silyl]propyl}phenylboronic acid is made by the method of Casado and Stobart (Casado, M. A.; Stobart, S. R., Org. Lett., 2 (11), 2000, 1549-1552). 4-{3-[diallyl(methyl)silyl]propyl}phenylboronic acid (0.576 g) and a solution of Pd(Ph3)4 (58 mg) in 5 mL of degassed toluene is placed in a 50 mL Schlenk tube. The mixture is purged with nitrogen, after which a solution of 4-bromo-7-phenyl-1,10-phenanthroline (0.670 g) and Na2CO3 (428 mg, 4 mmol) in 5 mL of degassed 4:1 H2O/CH3OH is added. The mixture is heated under nitrogen at 100° C. with rapid stirring until TLC monitoring shows the reaction to be complete (ca 24 hrs). The reaction mixture is then added to a separatory funnel and washed with ether (3×50 mL). The combined organic fractions are dried over MgSO4 and concentrated by roto-evaporation. The desired product is purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane.

Provenance & Evidence