A one-pot synthesis and functionalization of polyynes.
[reaction: see text] 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.
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Yasuhiro
Y
Morisaki
Thanh
T
Luu
Rik R
RR
Tykwinski