Skip to main content
Open Access Publications from the University of California


UCLA Previously Published Works bannerUCLA

Anodic oxidation triggered divergent 1,2- and 1,4-group transfer reactions of β-hydroxycarboxylic acids enabled by electrochemical regulation.


We report a set of electrochemically regulated protocols for the divergent synthesis of ketones and β-keto esters from the same β-hydroxycarboxylic acid starting materials. Enabled by electrochemical control, the anodic oxidation of carboxylic acids proceeded in either a one-electron or a two-electron pathway, leading to a 1,4-aryl transfer or a semipinacol-type 1,2-group transfer product with excellent chemoselectivity. The 1,4-aryl transfer represents an unprecedented example of carbon-to-oxygen group transfer proceeding via a radical mechanism. In contrast to previously reported radical group transfer reactions, this 1,4-group transfer process features the migration of electron-rich aryl substituents. Furthermore, with these chemoselective electrochemical oxidation protocols, a range of ketones and β-keto esters including those possessing a challenging-to-access medium-sized ring could be synthesized in excellent yields.

Many UC-authored scholarly publications are freely available on this site because of the UC's open access policies. Let us know how this access is important for you.

Main Content
For improved accessibility of PDF content, download the file to your device.
Current View