A rapid and efficient synthetic route to terminal aryl-acetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols

Tetrabutylammonium hydroxide with methanol as an additive was found to be a highly active catalyst for the cleavage of 4-aryl-2methyl-3-butyn-2-ols. The reaction was performed at 55-75 degrees C and gave terminal arylacetylenes in good to excellent yields within several minutes. Compared with the usual reaction conditions (normally > 110 degrees C, several hours), this novel catalyst system can dramatically decrease the reaction time under much milder conditions.