2-Cyanophenylzinc bromide

B. 4-Cyanophenylzinc bromide. A dry, 250-mL, three-necked flask equipped with... 

ETHYL 3-(p-CYAN0PHENYL)PR0PI0NATE FROM ETHYL 3-IODOPROPIONATE AND p-CYANOPHENYLZINC BROMIDE... 

Preparation of 4-cyanophenylzinc bromide by transmetallation and its reaction with phosphorus trichloride preparation of tris (4-cyanophenyl)phosphine-borane complex8... 

To a solution of Pd(dba)2 (163 mg, 0.3 mmol, 5mol%) in THF (4mL) was added dppf (125 mg, 0.3 mmol, 5 mol%) at 0°C. After a few minutes, phenyl triflate (0.91 g, 4 mmol) was added, followed by a solution of 4-chlorophenylzinc bromide (6 mmol) in THF/hexane prepared as described for 4-cyanophenylzinc bromide above. The reaction mixture was heated to 60 °C for 1.5 h then, after cooling to rt, it was worked up as usual and the crude residue obtained after evaporation of the solvents was purified by flash chromatography (hexanes), affording the biphenyl 58 as a clear oil (695 mg, 92% yield). 

---