Benzonitrile → Diphenylacetylene

Participants

Reaction Conditions

Reaction Steps

A solution of phenylethynylmagnesium bromide (4.0 ml; 4.00 mmol; 1.0 M in THF) in was treated at room temperature with a solution of ZnBr2 (0.473 g; 2.10 mmol) in THF (1 ml) and stirred for 30 min. This solution was then added to a room temperature solution of benzonitrile (0.204 ml; 0.206 g; 2.00 mmol), dichlorobis(trimethylphosphine)nickel (0.0282 g; 5 mol %), and tridecane (0.244 ml; 0.184 g; 1.00 mmol) in THF (1 ml). The reaction mixture was then heated to 65° C. and stirred for 46 h; then a sample was withdrawn and quenched in a mixture of 1 M sodium citrate (aq) and MTBE. GC analysis of the organic phase of the hydrolyzed reaction sample showed the presence of 0.63 mmol (31% yield) of diphenylacetylene and 0.36 mmol of benzonitrile remaining in the reaction mixture.

Provenance & Evidence