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. 2007 Apr 27;72(9):3558-60.
doi: 10.1021/jo070130r. Epub 2007 Apr 5.

Ozonolysis of unsaturated organotrifluoroborates

Gary A Molander  1 , David J Cooper
Affiliations

Ozonolysis of unsaturated organotrifluoroborates

Gary A Molander et al. J Org Chem. .

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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Figures

Figure 1
Figure 1
Transformation to Product from Carbonyl Oxides (I) vs. Secondary Ozonides (II).
See this image and copyright information in PMC

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