PhI(OAc)2-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

Dong-Fang Jiang; Zhenjie Qi; Dengfeng Li; Si-Miaomiao Wen; Zhao Liu; Wen-Juan Hao; Bo Jiang

doi:10.1039/D3OB01125A

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PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor†

Dong-Fang Jiang,

‡*^a Zhenjie Qi,

‡^b Dengfeng Li,‡^a Si-Miaomiao Wen,^a Zhao Liu,^a Wen-Juan Hao

^c and Bo Jiang

*^c

Author affiliations

* Corresponding authors

^a Hunan Provincial Key Laboratory of the Research and Development of Novel Pharmaceutical Preparations, Changsha Medical University, Provincial First-Class Applied Discipline (Pharmacy), Changsha, China
E-mail: dg1824035@smail.nju.edu.cn

^b Department of Engineering, Jining University, Qufu, Shandong, P. R. China
E-mail: 202310001@jnxy.edu.cn

^c School of Chemistry & Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China
E-mail: jiangchem@jsnu.edu.cn

Abstract

A metal-free protocol for the direct construction of C(sp²)–N and C–O bonds via a PhI(OAc)₂-mediated dehydrogenative aminoacyloxylation of β,γ-unsaturated hydrazones with Togni reagent II is reported. Initiated by the carboxyl-containing species generated in situ from Togni reagent II, this method offers a new solution for regioselective functionalization at a remote site on β,γ-unsaturated hydrazones, thus providing a straightforward method for the synthesis of acyloxyl-substituted pyridazines. This reaction features a broad substrate scope and mild conditions.

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Article information

DOI: https://doi.org/10.1039/D3OB01125A
Article type: Paper
Submitted: 14 Jul 2023
Accepted: 06 Aug 2023
First published: 10 Aug 2023

Download Citation

Org. Biomol. Chem., 2023,21, 6757-6761

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PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

D. Jiang, Z. Qi, D. Li, S. Wen, Z. Liu, W. Hao and B. Jiang, Org. Biomol. Chem., 2023, 21, 6757 DOI: 10.1039/D3OB01125A

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Organic & Biomolecular Chemistry