Electro-Activation of C–H Bonds

  • Author: Elliot Steeples
  • Published Date: 19 August 2017
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Electro-Activation of C–H Bonds

Related Societies

Electrochemical bond activation is a field of study that has recently gained momentum. The use of mild conditions and non-stoichiometric additives make electrochemical organic syntheses interesting for the sustainable and green chemistry communities. Recently reported examples have focused on the activation of aromatic bonds using nitrogen heterocycles and bases, notably including C–N and C–H activations for the synthesis of oxazoles.

Sigfried Waldvogel, University of Mainz, Germany, and colleagues have used electrochemical C–H activation for the synthesis of a series of benzoxazinones. The reaction involves the oxidative activation of an aryl C–H bond, using pyridine as a base. This is carried out using a phenoxyacetate starting material, and the C–H bond is activated in the ortho position relative to the ester group.

A number of different phenoxyacetate substrates of varying electronic and steric properties could be successfully activated. Good to excellent yields were obtained using a current density of 10 mA cm–2, although moderate conversion could also be performed using just 1 mA cm–2. The final ring-closure step was carried out through a condensation using piperidine, thereby producing the cyclic amide group. This approach is a convenient method of accessing various different benzoxazinone structures, which are common heterocyclic motifs found in pharmaceutical products.


Article Views: 2076

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH