Chemoselective Aliphatic C-H Bond Oxidation Enabled by Polarity Reversal.

ABSTRACT: Methods for selective oxidation of aliphatic C-H bonds are called on to revolutionize organic synthesis by providing novel and more efficient paths. Realization of this goal requires the discovery of mechanisms that can alter in a predictable manner the innate reactivity of these bonds. Ideally, these mechanisms need to make oxidation of aliphatic C-H bonds, which are recognized as relatively inert, compatible with the presence of electron rich functional groups that are highly susceptible to oxidation. Furthermore, predictable modification of the relative reactivity of different C-H bonds within a molecule would enable rapid diversification of the resulting oxidation products. Herein we show that by engaging in hydrogen bonding, fluorinated alcohols exert a polarity reversal on electron r

SUBMITTER: Dantignana V 

PROVIDER: S-EPMC5746866 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature