Pyrene, 1,6-Dibromo- → 1,6-Diisobutylpyrene

Participants

Reaction Steps

A mixture of 1,6-dibromopyrene (15.13 g, 42.0 mmol), isobutyl boronic acid (27.58 g, 270 mmol), potassium phosphate tribasic monohydrate (53.94 g, 254 mmol), Pd2(dba)3 (3.02 g, 3.30 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.00 g, 2.45 mmol) in toluene (300 mL) was fully degassing by bubbling through with nitrogen. The reaction mixture was maintained at reflux under nitrogen for 16 h. The reaction mixture was cooled, then filtered through a pad of Celite and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using hexane to yield 1,6-diisobutylpyrene (10.18 g, 77% yield) as a white solid.

Provenance & Evidence