Lenhard Marola S, Winter Johannes, Sandvoß Alexander, Gálvez-Vázquez María de Jesús, Schollmeyer Dieter, Waldvogel Siegfried R
Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
Karlsruhe Institute of Technology (KIT), Institute of Biological and Chemical Systems - Functional Molecular Systems (IBCS-FMS), Kaiserstraße 12, 76131 Karlsruhe, Germany.
Org Biomol Chem. 2025 Mar 5;23(10):2391-2399. doi: 10.1039/d4ob01875c.
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.
建立了一种可持续、通用且可扩展的电化学方法,通过对广泛可得的硝基芳烃进行阴极还原直接制备3-(酰氨基烷基)-2,1-苯并异恶唑。该方法的特点是在恒流条件下采用简单的无隔膜装置、廉价且可重复使用的碳基电极以及环境友好的反应条件。在39个高度多样化的实例中验证了该方法的通用性,产率高达81%。50倍的放大电解突出了其在制备应用中的实用性。