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Updated: Mar 18, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
An Iminium Salt Organocatalyst for Selective Aliphatic C-H Hydroxylation
Daoyong Wang1, William G Shuler1, Conor J Pierce1
1Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
Abstract:
The first examples of catalysis of aliphatic C-H hydroxylation by an iminium salt are presented. The method allows the selective organocatalytic hydroxylation of unactivated 3° C-H bonds at room temperature using hydrogen peroxide as the terminal oxidant. Hydroxylation of an unactivated 2° C-H bond is also demonstrated. Furthermore, improved functional group compatibility over other catalytic methods is reported in the form of selectivity for aliphatic C-H hydroxylation over alcohol oxidation. On the basis of initial mechanistic studies, an oxaziridinium species is proposed as the active oxidant.
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