Simple and Versatile Electrochemical Synthesis of Highly Substituted 2,1-Benzisoxazoles

17 October 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A sustainable, general and scalable electrochemical protocol for the 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 38 highly diverse examples with up to 81% yield. A 50-fold scale-up electrolysis highlights its relevance for preparative applications.

Keywords

Electrochemistry
Benzisoxazole
Nitro Reduction
Heterocycles

Supplementary materials

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The ESI contains experimental and analytical data (NMR, CV studies and HRMS).
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