Electrosynthesis of Aryliminophosphoranes in Continuous Flow

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 electroly...

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Veröffentlicht in:Advanced synthesis & catalysis 2024-02, Vol.366 (4), p.955-960
Hauptverfasser: Costa e Silva, Rodrigo, Vega, Clara, Regnier, Morgan, Capaldo, Luca, Wesenberg, Lars, Lowe, Grace, Thiago de Oliveira, Kleber, Noël, Timothy
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container_end_page 960
container_issue 4
container_start_page 955
container_title Advanced synthesis & catalysis
container_volume 366
creator Costa e Silva, Rodrigo
Vega, Clara
Regnier, Morgan
Capaldo, Luca
Wesenberg, Lars
Lowe, Grace
Thiago de Oliveira, Kleber
Noël, Timothy
description 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.
doi_str_mv 10.1002/adsc.202300635
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subjects Amides
Amines
Aniline
Aromatic compounds
Continuous flow
flow electrochemistry
Functional groups
iminophosphoranes
Isocyanates
nitroarenes
paired electrolysis
Synthesis
undivided cell
title Electrosynthesis of Aryliminophosphoranes in Continuous Flow
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