Catechol → Diphenylacetylene

Participants

Reaction Steps

A solution of catechol (0.440 g; 4.00 mmol) in THF (2 ml) was treated at 0° C. with diethylzinc (4 ml; 4.00 mmol; 1.0 M in THF) and the resulting solution was allowed to warm to room temperature for 20 min. Solvent was removed in vacuo, then phenylethynyllithium (4.0 ml; 4.00 mmol; 1.0 M THF) was added at room temperature and the resulting mixture was stirred for 30 min. This solution was then added to a room temperature mixture 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). The reaction mixture was then heated to 65° C. and stirred for 6 days; then a sample was withdrawn and quenched in a mixture of 1 M sodium citrate (aq) and MTBE.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 1.08 mmol (54% yield) of diphenylacetylene and 0.41 mmol of benzonitrile remaining in the reaction mixture.

Provenance & Evidence