Electrosynthesis of Aryliminophosphoranes in Continuous Flow

Author(s)

Costa e Silva, Rodrigo ; Vega, Clara ; Regnier, Morgan ; Capaldo, Luca ; Wesenberg, Lars ; Lowe, Grace ; de Oliveira, Kleber Thiago ; Noel, Timothy

• Document type: Journal article
• Source: ADVANCED SYNTHESIS & CATALYSIS; v. N/A, p. 7-pg., 2023-08-09.

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. (AU)

• FAPESP's process: 18/00879-6 - Arylation reactions of heterocycles photocatalysed by porphyrins in both batch and continuous flow conditions.
• Grantee: Rodrigo Costa e Silva
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 20/06874-6 - Applications of technologies and synthetic methodologies developed under continuous flow conditions at LQBO-UFSCar for the preparation of molecules with biological activities and APIs
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants
• FAPESP's process: 21/09145-8 - Synthesis of Iminophosphoranes from nitroarenes by an electrochemical approach
• Grantee: Rodrigo Costa e Silva
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate