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

Rit, Raja K. ; Yadav, M. Ramu ; Sahoo, Akhila K. (2012) Pd(II)-Catalyzed Primary-C(sp3)–H Acyloxylation at Room Temperature Organic Letters, 14 (14). pp. 3724-3727. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/ol301579q

Related URL: http://dx.doi.org/10.1021/ol301579q

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:122457
Deposited On:02 Aug 2021 16:39
Last Modified:02 Aug 2021 16:39

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