One-shot double elimination process: a practical and concise protocol for diaryl acetylenes

A variety of diaryl acetylenes were obtained in good yields when lithium hexamethyldisilazide was added to a solution of arylmethyl sulfone, aryl aldehyde, and chlorodiethylphosphate in THF. In this one-shot process, a number of transformations such as aldol reaction, phosphorylation of aldolate, and double elimination of the resulting beta-substituted sulfone proceeded successively to afford the desired acetylenes. The one-shot process was accelerated by the substitution of halogen atoms on the phenyl groups, and unsymmetrically substituted diaryl acetylenes were obtained without contamination of the dehalogenated products. Diaryl acetylenes with other substituents such as CF3, ethoxycarbonyl, dimethylamino, TMS-acetylene groups, as well as pyridinyl and thienyl moieties were also accessible with this method. However, methoxy-substituted compounds were obtained in moderate yields under the same conditions, but the yields were increased when lithium diisopropylamide was used instead.