Pd(II)-Catalyzed Primary-C(sp3)–H Acyloxylation at Room Temperature

With the aid of a novel S-methyl-S-2-pyridyl-sulfoximine (MPyS) directing group (DG), the unactivated primary β-C(sp3)–H bond of MPyS-N-amides oxidizes at room temperature. The catalytic conditions are applicable to the diacetoxylation of primary β,β′-C(sp3)–H bonds, and the carboxylic acid solvent...

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Bibliographic Details
Published in:Organic letters 2012-07, Vol.14 (14), p.3724-3727
Main Authors: Rit, Raja K, Yadav, M. Ramu, Sahoo, Akhila K
Format: Article
Language:English
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Summary:With the aid of a novel S-methyl-S-2-pyridyl-sulfoximine (MPyS) directing group (DG), the unactivated primary β-C(sp3)–H bond of MPyS-N-amides oxidizes at room temperature. The catalytic conditions are applicable to the diacetoxylation of primary β,β′-C(sp3)–H bonds, and the carboxylic acid solvent is pivotal in the formation of the C–O bond. The MPyS-DG cleaves from the oxidation products and is recovered. This method provides convenient access to α,α′-disubstituted-β-hydroxycarboxylic acids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol301579q