Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation.

ABSTRACT: Electronegative substituents arrayed in 1,3-relationships along saturated carbon frameworks can exert strong influence over molecular conformation due to dipole minimization effects. Simple and general methods for incorporation of such functional group relationships could thus provide a valuable tool for modulating molecular shape. Here, we describe a general strategy for the 1,3-oxidation of cyclopropanes using aryl iodine(I-III) catalysis, with emphasis on 1,3-difluorination reactions. These reactions make use of practical, commercially available reagents and can engage a variety of substituted cyclopropane substrates. Analysis of crystal and solution structures of several of the products reveal the consistent effect of 1,3-difluorides in dictating molecular conformation. The generality

SUBMITTER: Banik SM 

PROVIDER: S-EPMC5671765 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature