Ozonolysis of unsaturated organotrifluoroborates.
Organotrifluoroborates are robust reagents capable of withstanding ozonolysis of remote alkenes, thus providing a new route to oxo-substituted organotrifluoroborates. The primary ozonides initially generated upon ozonolysis can be reduced with Zn/AcOH to afford the carbonyl compounds. Alternatively, capture of the carbonyl oxides with either an appropriate N-oxide or H2O easily gives the desired oxo-substituted organotrifluoroborates. Both unsaturated alkyltrifluoroborates and aryltrifluoroborates effectively participate in the reaction. The process provides oxo-functionalized organotrifluoroborates that cannot be prepared directly via either transmetalation or hydroboration protocols.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Cooper
David J
DJ
D001881:Borates / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D010126:Ozone / Q000737:chemistry*
D001881:Borates; D006845:Hydrocarbons, Fluorinated; D010126:Ozone