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Updated: Aug 11, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
A one-pot synthesis and functionalization of polyynes
Yasuhiro Morisaki1, Thanh Luu, Rik R Tykwinski
1Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
This study presents a novel one-pot method for synthesizing functionalized diynes and triynes from dibromoolefins. The versatile approach allows for diverse derivatization via in situ trapping or palladium-catalyzed cross-coupling reactions.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Polyyne frameworks are crucial in various chemical applications.
- Efficient synthesis of functionalized diynes and triynes remains a challenge.
Purpose of the Study:
- To develop a versatile one-pot method for synthesizing functionalized diynes and triynes.
- To explore divergent derivatization pathways from a common intermediate.
Main Methods:
- Carbenoid rearrangement of dibromoolefin precursors to form polyyne frameworks.
- In situ trapping of Li-acetylide intermediates with electrophiles.
- Transmetalation to Zn- or Sn-acetylides followed by palladium-catalyzed cross-coupling reactions.
Main Results:
- Successful one-pot synthesis and derivatization of diynes and triynes.
- Generation of functionalized di- and triynes via electrophilic trapping.
- Divergent synthesis of diaryl polyynes and aryl ynones through cross-coupling.
Conclusions:
- The reported method offers a streamlined and efficient route to diverse polyyne structures.
- The strategy enables access to complex molecules through versatile derivatization.
- This work expands the synthetic toolbox for polyyne chemistry.
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