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Catalytic C–C coupling of diazo compounds with arylboronic acids: using surface modified sewage sludge as catalyst

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Abstract

A green, mild and efficient synthesis of diarylmethines using sewage sludge-derived carbonaceous materials (SW) by perchloric acid catalyzed coupling reactions between diazo compounds and arylboronic acids was developed. The reaction shows a high level of functional tolerance and a broad substrate scope. Furthermore, the highly selective 1,2-alkyl shift products were furnished through the sterically demanding R4, R5 migration of diazo compounds (3-diazochromanone). The structures of 1,2-shift products have been further confirmed by single-crystal X-ray analysis. Significantly, the synthesis of the core structures of darifenacin (a clinical drug for overactive bladder syndrome, OAB) and diclofensine (a stimulant drug showing antidepressant and monoamine reuptake inhibitor activity) further demonstrated the efficacy and synthetic potential of this method.

Graphical abstract: Catalytic C–C coupling of diazo compounds with arylboronic acids: using surface modified sewage sludge as catalyst

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Supplementary files

Article information


Submitted
25 Jan 2020
Accepted
17 Apr 2020
First published
27 Apr 2020

Green Chem., 2020, Advance Article
Article type
Paper

Catalytic C–C coupling of diazo compounds with arylboronic acids: using surface modified sewage sludge as catalyst

Z. Zhang, Y. Yu, Y. Xie, T. Hughes, J. Xu, F. Huang and H. Huang, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC00317D

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