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[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.
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Morisaki et al. (2006) studied this question.
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