Metal-free synthesis of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts.
Ynones are a valuable functional group and building block in organic synthesis. Ynones serve as a precursor to many important organic functional groups and scaffolds. Traditional methods for the preparation of ynones are associated with drawbacks including harsh conditions, multiple purification steps, and the presence of unwanted byproducts. An alternative method for the straightforward preparation of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts is described herein. The adoption of organotrifluoroborate salts as an alternative to organometallic reagents for the formation of new carbon-carbon bonds has a number of advantages. Potassium organotrifluoroborate salts are shelf stable, have good functional group tolerance, low toxicity, and a wide variety are straightforward to prepare. The title reaction proceeds rapidly at ambient temperature in the presence of a Lewis acid without the exclusion of air and moisture. Fair to excellent yields may be obtained via reaction of various aryl and alkyl acid chlorides with alkynyltrifluoroborate salts in the presence of boron trichloride.
Faculty of Science, University of Ontario Institute of Technology.
Cassandra L
CL
Taylor
Faculty of Science, University of Ontario Institute of Technology; Yuri.Bolshan@uoit.ca.
Yuri
Y
Bolshan
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D002712:Chlorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008670:Metals / Q000737:chemistry
D000480:Alkynes; D001880:Boranes; D001897:Boronic Acids; D002712:Chlorides; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D008670:Metals; C092267:boron trichloride