Ozonolysis of unsaturated organotrifluoroborates |
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Authors: | Molander Gary A Cooper David J |
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Institution: | Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu |
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Abstract: | 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. |
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