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Synlett
DOI: 10.1055/a-2615-0057
letter

Thiourea Dioxide-Mediated N−O Bond Cleavage in Hydroxamic Acids for the Selective Synthesis of Primary Amides

Yiyong Zhao
1   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou, China (Ringgold ID: RIN12624)
,
Jianxuan Zhang
1   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou, China (Ringgold ID: RIN12624)
,
Jianxin Miao
1   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou, China (Ringgold ID: RIN12624)
,
Shuting Ge
2   College of Chemical Engineering, Zhejiang Environment Technology Co Ltd, Hangzhou, China
,
Guofu Zhang
3   Zhejiang University of Technology, College of Chemical Engineering and Materials Science, hangzhou, China
,
chengrong Ding 
4   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, China
,
Jinghui lyu
5   College of Chemical Engineering, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, China
,
Xiaonian Li
6   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou, China
› Author AffiliationsSupported by: National Natural Science Foundation of China NSFC22278368
Supported by: Zhejiang Provincial Natural Science Foundation LY21B060006
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Thiourea dioxide (TDO), a sustainable and cost-effective industrial compound, has been demonstrated as a bifunctional reagent for efficient hydroxyl activating and N-O bond cleavage of hydroxamic acids enabling the efficient synthesis of primary amides with excellent functional group compatibility. This straightforward process has been successfully applied to gram-scale synthesis of niacinamide. Furthermore, mechanistic studies suggested that the N-O bond cleavage involves a cascade process of sulfenylation and reduction. This novel and robust transformation gives a new lease of the synthetic utility of TDO as an innocuous and versatile reagent in organic chemistry.



Publication History

Received: 27 March 2025

Accepted after revision: 16 May 2025

Accepted Manuscript online:
16 May 2025

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