Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach.
A number of alkynyl pinacolboronates bearing various functional groups were synthesized according to literature methods. These were then stereoselectively reduced to the cis-alkenyl pinacolboronates via hydroboration with dicyclohexylborane followed by chemoselective protodeboronation using acetic acid. Treatment with potassium hydrogen fluoride smoothly converted these to the corresponding potassium organotrifluoroborates.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Ellis
Noel M
NM
D019342:Acetic Acid / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis*; D001881:Borates / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D006858:Hydrofluoric Acid / Q000737:chemistry; D008956:Models, Chemical; D011188:Potassium / Q000737:chemistry*; D017680:Potassium Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D001881:Borates; D001897:Boronic Acids; D006845:Hydrocarbons, Fluorinated; D017680:Potassium Compounds; C077003:potassium hydrogen fluoride; D019342:Acetic Acid; D006858:Hydrofluoric Acid; D011188:Potassium