A One-Pot Synthesis and Functionalization of Polyynes

Abstract

A one-pot synthesis and derivatization of diynes and triynes is reported. The polyyne framework is formed from a dibromoolefin precursor based on a carbenoid rearrangement, and the resulting Li−acetylide is then trapped in situ with an electrophile to provide functionalized di- and triynes. Alternatively, transmetalation of the Li−acetylide intermediate provides either the Zn− or Sn−acetylide, which then allows for the divergent preparation of diaryl polyynes or aryl ynones via palladium-catalyzed cross-coupling reactions