Simple and versatile electrochemical synthesis of highly substituted 2,1-benzisoxazoles
A sustainable, general and scalable electrochemical protocol for direct access to 3-(acylamidoalkyl)-2,1-benzisoxazoles by cathodic reduction of widely accessible nitro arenes is established. The method is characterised by a simple undivided set-up under constant current conditions, inexpensive and reusable carbon-based electrodes, and environmentally benign reaction conditions. The versatility of the developed protocol is demonstrated on 39 highly diverse examples with up to 81% yield. A 50-fold scale-up electrolysis highlights its relevance for preparative applications.
Authors
- Alexander Sandvoß (ORCID: https://orcid.org/0000-0002-2456-5597)
- Marola S. Lenhard
- Siegfried R. Waldvogel (ORCID: https://orcid.org/0000-0002-7949-9638)
- María de Jesús Gálvez‐Vázquez (ORCID: https://orcid.org/0000-0002-0416-6556)
- J. Winter (ORCID: https://orcid.org/0000-0001-9307-1497)
- Dieter Schollmeyer
Institutions
- Karlsruhe Institute of Technology (DE)
- Johannes Gutenberg University Mainz (DE)
- Max Planck Institute for Chemical Energy Conversion (DE)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2024-12-03
- DOI
- https://doi.org/10.1039/d4ob01875c
- Citations
- 4
- Primary Topic
- Inorganic and Organometallic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Science Foundation
- Deutscher Akademischer Austauschdienst
- Deutsche Forschungsgemeinschaft
- Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
- Max-Planck-Gesellschaft