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Electrosynthesis of Aryliminophosphoranes in Continuous Flow |
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| Authors: | Rodrigo Costa e Silva Clara Vega Morgan Regnier Luca Capaldo Lars Wesenberg Grace Lowe Kleber Thiago de Oliveira Timothy Noël |
| Affiliation: | 1. Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands Departamento de Química, Universidade Federal de Sao Carlos, SP, 13565-905 Brazil These authors contributed equally to this work.;2. Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands These authors contributed equally to this work.;3. Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands;4. Departamento de Química, Universidade Federal de Sao Carlos, SP, 13565-905 Brazil |
| Abstract: | A practical electrochemical method for synthesizing aryliminophosphoranes from widely available nitro(hetero)arenes in a continuous-flow system is presented. The utilization of flow technology offers several advantages to our approach, including the elimination of the need for a supporting electrolyte and enhanced scalability. Our method demonstrates good tolerance towards various functional groups, with electron-deficient nitroarenes being particularly suitable for this strategy. In addition, we have demonstrated the versatility of aryliminophosphoranes as intermediates in synthesizing anilines, amines, and amides. To further enhance the utility of our approach, we have developed a telescoped method that utilizes a tube-in-tube setup for the in-situ production of isocyanates. |
| Keywords: | iminophosphoranes flow electrochemistry nitroarenes paired electrolysis undivided cell |