[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:20](B(O)O)[CH2:21][CH2:22][CH3:23]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]A 4 mL vial was charged with 4-tert-butylbromobenzene (213 mg, 1.00 mmol), Pd(dba)2 (5.8 mg, 0.01 mmol, 1 mol %), Ph5FcP(t-Bu)2 (14.2 mg, 0.02 mmol, 2 mol %), K3PO4 (430 mg, 2.02 mmol, powdered) and n-butylboronic acid (124 mg, 1.21 mmol). Anhydrous toluene (2 mL) and a stirring bar were added, and the vial was then sealed with a cap containing a PTFE septum and removed from the drybox. The reaction mixture was stirred at 100° C. for 2.5 h. After the starting aryl halide was consumed as determined by GC, the reaction solution was cooled to room temperature. The reaction solution was then adsorbed onto silica gel directly, and the product was isolated by eluting with ethyl acetate/hexanes to give 175 mg (92%) of 4-tert-butyl-1-n-butylbenzene as colorless oil. Kugelrohl distillation was used for further purification.
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