A deacetonative Sonogashira coupling of aryl chlorides and propargyl alcohols

Organic Chemistry Periodically

While sp-sp2 couplings are now classics, whether using terminal alkynes, zinc, magnesium, boron or silicon alkynides, it is the first time I see a propargyl alcohol used as a partner in this type of coupling. The group of Yang and Wu (Zhengzhou University, China) reported last year a deacetonative “Sonogashira” coupling between aryl chlorides and tertiary propargyl alcohols:

13aIf you know your Name Reactions really well, it should remind you of the retro-Favorskii reaction, named after the Favorskii reaction (or Favorskii-Babayan reaction, see Scheme below), not to be confused with the Favorskii rearrangement.

13bReference: J. Org. Chem.2013 10506-10511 link

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