Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Insights into the Mechanism of Anodic N–N Bond Formation by Dehydrogenative Coupling

Insights into the Mechanism of Anodic N–N Bond Formation by Dehydrogenative Coupling
Kevin D. Moeller, Tile Gieshoff, Anton Kehl, Siegfried R. Waldvogel, Dieter Schollmeyer
The electrochemical synthesis of pyrazolidine-3,5-diones and benzoxazoles by N–N bond formation and C,O linkage, respectively, represents an easy access to medicinally relevant structures. Electrochemistry as a key technology ensures a safe and sustainable approach. We gained insights in the mechanism of these reactions by combining cyclovoltammetric and synthetic studies. The electron-transfer behavior of anilides and dianilides was studied and led to the following conclusion: The N–N bond formation involves a diradical as intermediate, whereas the benzoxazole formation is based on a cationic mechanism. Besides these studies, we developed a synthetic route to mixed dianilides as starting materials for the N–N coupling. The compatibility with valuable functionalities like triflates and mesylates for follow-up reactions as well as the comparison of different electrochemical set-ups also enhanced the applicability of this method.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07488

DOI: 10.1021/jacs.7b07488

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.