Jump to main content
Jump to site search

Issue 2, 2014
Previous Article Next Article

Organocatalytic C–H hydroxylation with Oxone® enabled by an aqueous fluoroalcohol solvent system

Author affiliations

Abstract

Selective hydroxylation of 3° and benzylic C–H bonds is made possible using a non-metal-based catalyst system, Oxone as the terminal oxidant, and an aqueous fluoroalcohol solvent mixture. The choice of solvent is uniquely effective for this process, but seemingly at odds with our finding that H2O promotes reduction of the oxaziridine intermediate. Our studies suggest that the hydroxylation reaction is occurring within a fluoroalcohol microdroplet, which both concentrates the reactants and mitigates the deleterious impact of H2O on oxaziridine stability. These discoveries have led to demonstrable improvements in the organocatalytic oxygenation of hydrocarbon substrates and, for the first time, the successful use of Oxone with this catalyst system. Reactions generally afford product and unreacted starting material in near quantitative amounts and display outstanding selectivity for 3° and benzylic C–H bond oxidation.

Graphical abstract: Organocatalytic C–H hydroxylation with Oxone® enabled by an aqueous fluoroalcohol solvent system

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 21 Sep 2013, accepted on 01 Nov 2013 and first published on 22 Nov 2013


Article type: Edge Article
DOI: 10.1039/C3SC52649F
Citation: Chem. Sci., 2014,5, 656-659
  •   Request permissions

    Organocatalytic C–H hydroxylation with Oxone® enabled by an aqueous fluoroalcohol solvent system

    A. M. Adams and J. Du Bois, Chem. Sci., 2014, 5, 656
    DOI: 10.1039/C3SC52649F

Search articles by author