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

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) p...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 16; pp. 4131 - 4138
Main Authors Yang, Zhifang, Du, Feng-Huan, Zhang, Chi, Du, Yunfei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 08.08.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BORONIC ACIDS
SODIUM-AZIDE
C-H AZIDATION
ONE-POT SYNTHESIS
REGIOSELECTIVE SYNTHESIS
CHEMISTRY
STABLE AZIDOIODINANES
BETA-KETO-ESTERS
COMBINATION
TRIMETHYLSILYL AZIDE
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Summary: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.
ISSN:2052-4129
DOI:10.1039/d3qo00732d