Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


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

Supplementary files

Article information


Submitted
21 Sep 2013
Accepted
01 Nov 2013
First published
22 Nov 2013

Chem. Sci., 2014,5, 656-659
Article type
Edge Article

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

Social activity

Search articles by author

Spotlight

Advertisements