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Ozonolysis of unsaturated organotrifluoroborates.

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.

SUBMITTER: Molander GA

PROVIDER: S-EPMC2504467 | biostudies-literature | 2007 Apr

REPOSITORIES: biostudies-literature

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Ozonolysis of unsaturated organotrifluoroborates.

Molander Gary A GA Cooper David J DJ

The Journal of organic chemistry 20070405 9

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 aryltrifluoroborat ...[more]

PMID: 17408287

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