Functionalization of unactivated aliphatic C-H bonds is utilized in a wide array of biosynthetic pathways.  Though nature takes full advantage of this remarkable transformation, current synthetic methods are limited and often lack selectivity and efficiency.  In order to enable a broader approach to the synthesis of natural products, pharmaceuticals, and fine chemicals, novel methods for conversion of typically unreactive aliphatic C-H bonds are necessary.  Herein, we report mild conditions for the hydroxylation of aliphatics via controlled radical translocation and subsequent oxidation to carbocation.  Employment of visible-light photoredox catalysis at room temperature together with the Tzo directing group facilitates site-selective replacement of relatively inert C-H bonds with the synthetically useful C-OH.

Photocatalytic C-H activation: Directed hydroxylation of unactivated aliphatics

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.