Issue 16, 2023

Accessing aryl azides via copper powder-catalyzed cross-coupling of arylboronic acids with the hypervalent azido-iodine reagent ABZ(I)

Abstract

The cross-coupling reaction of arylboronic acids with the hypervalent azido-iodine reagent ABZ(I) in the presence of a catalytic amount of copper powder was found to give aryl azides in high yields. This transformation is ligand- and base-free and has a good functional group tolerance, with ABZ(I) playing a bifunctional role as an oxidant and an azido source. DFT calculations were performed to obtain mechanistic insights into this transformation.

Graphical abstract: Accessing aryl azides via copper powder-catalyzed cross-coupling of arylboronic acids with the hypervalent azido-iodine reagent ABZ(I)

Supplementary files

Article information

Article type
Research Article
Submitted
16 May 2023
Accepted
12 Jul 2023
First published
14 Jul 2023

Org. Chem. Front., 2023,10, 4131-4138

Accessing aryl azides via copper powder-catalyzed cross-coupling of arylboronic acids with the hypervalent azido-iodine reagent ABZ(I)

Z. Yang, F. Du, C. Zhang and Y. Du, Org. Chem. Front., 2023, 10, 4131 DOI: 10.1039/D3QO00732D

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