Ruthenium-catalyzed hydroxylation of unactivated tertiary C-H bonds.

Abstract

The combination of catalytic RuCl(3) and pyridine with KBrO(3) as the stoichiometric oxidant is shown to efficiently promote the hydroxylation of unactivated tertiary C-H bonds. Substrates possessing different polar functional groups--ester, epoxide, sulfone, oxazolidinone, carbamate, and sulfamate--are found to engage in this reaction to give alcohol products in yields generally exceeding 50%. As judged based on efficiency, ease of operation, substrate scope, and selectivity toward tertiary C-H centers, the method appears competitive with other C-H hydroxylation processes.

DOI: 10.1021/ja1046999

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Cite this paper

@article{McNeill2010RutheniumcatalyzedHO, title={Ruthenium-catalyzed hydroxylation of unactivated tertiary C-H bonds.}, author={Eric McNeill and Justin Du Bois}, journal={Journal of the American Chemical Society}, year={2010}, volume={132 29}, pages={10202-4} }