One-pot and one-shot process for diarylethynes

ORGN 617

Akihiro Orita, orita@high.ous.ac.jp, Department of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama, Japan
A variety of diarylacetylenes were obtained in good yields by addition of LiHMDS to a THF solution of arylmethyl sulfone, arylaldehyde and chloro diethylphosphate. In this “one-shot process”, a number of transformations such as aldol reaction, phosphorylation of aldolate, and double elimination of the resulting ?-substituted sulfone proceeded successively to afford the desired acetylenes. This protocol was useful for preparation of diarylacetylenes bearing various functional groups such as halogens, CF3, ethoxycarbonyl, dimethylamino, TMS-acetylene groups as well as pyridinyl and thienyl moieties