Diazenylation of active methyne compounds via arylazo sulfones

A diazenylation reaction between active methyne compounds and arylazo sulfones is reported. The mild reaction involves an initial azotization, followed by a nucleophilic addition–elimination. The acyl group plays a dual role, acting as an electron-withdrawing substituent to activate the methyne site...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-05, Vol.11 (10), p.2815-2820
Main Authors: Wang, Ruiqing, Kong, Lingkai, Zong, Xinyu, Zhang, Minghui, Chen, Wenyi, Liu, Yaxin, Ma, Lingjuan, Zhao, Yulei
Format: Article
Language:English
Subjects:
Hydrazones
Ring opening
Sulfones
Online Access:Get full text
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Summary:A diazenylation reaction between active methyne compounds and arylazo sulfones is reported. The mild reaction involves an initial azotization, followed by a nucleophilic addition–elimination. The acyl group plays a dual role, acting as an electron-withdrawing substituent to activate the methyne site and as a readily leaving group to promote azo-rearrangement. The presented results shed light on a practical approach to synthesize hydrazones and will provide new possibilities for the late-stage ring-opening and diazenylation of complex molecules.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo00343h