title: An Iminium Salt Organocatalyst for Selective Aliphatic C-H Hydroxylation.
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.
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
authors.forename: Daoyong
authors.initials: D
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
authors.forename: William G
authors.initials: WG
authors.lastname: Shuler
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
authors.forename: Conor J
authors.initials: CJ
authors.lastname: Pierce
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.
authors.forename: Michael K
authors.initials: MK
authors.lastname: Hilinski