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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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-02, Vol.366 (4), p.955-960
Main Authors: Costa e Silva, Rodrigo, Vega, Clara, Regnier, Morgan, Capaldo, Luca, Wesenberg, Lars, Lowe, Grace, Thiago de Oliveira, Kleber, Noël, Timothy
Format: Article
Language:English
Subjects:
Amides
Amines
Aniline
Aromatic compounds
Continuous flow
flow electrochemistry
Functional groups
iminophosphoranes
Isocyanates
nitroarenes
paired electrolysis
Synthesis
undivided cell
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300635