Citation: Yadong Li, Feng-Huan Du, Junjie Li, Jun Xu, Zhifang Yang, Shanshan Li, Chi Zhang, Yunfei Du. Preparation of benziodazole-triflate and its application as both 2-iodobenzamido- and triflate-transfer reagents[J]. Chinese Chemical Letters, ;2025, 36(6): 110338. doi: 10.1016/j.cclet.2024.110338 shu

Preparation of benziodazole-triflate and its application as both 2-iodobenzamido- and triflate-transfer reagents

Yadong Li ^{a, 1} ,
Feng-Huan Du ^{b, 1} ,
Junjie Li ^b ,
Jun Xu ^a ,
Zhifang Yang ^a ,
Shanshan Li ^a ,
Chi Zhang ^{b, *,} ,
Yunfei Du ^{a, *,}

a.
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China
b.
State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

duyunfeier@tju.edu.cn

zhangchi@nankai.edu.cn

Received Date: 8 June 2024
Revised Date: 1 August 2024
Accepted Date: 12 August 2024
Available Online: 13 August 2024

Figures(8)

Benziodazole-triflate, as a novel heterocyclic hypervalent iodine(Ⅲ) reagent, was prepared from the reaction of hypervalent chloroiodine(Ⅲ) with silver triflate under mild conditions. The structure of this new reagent was elucidated by NMR spectroscopy and X-ray crystallography, and its reactions with diverse α-electron withdrawing group substituted carbonyl compounds were investigated. The results implied that benziodazole-triflate could be selectively used as both a 2-iodobenzamido-transfer reagent for the synthesis of oxazole compounds, and a triflate-transfer reagent for the triflation of β-keto-sulfones. Ionic mechanistic pathways, supported by density functional theory (DFT) calculations, were proposed to account for the divergent selectivities of the transformations.
- Benziodazole-triflate,
- 2-Iodobenzamido-transfer reagent,
- Oxidative cyclization,
- Triflate-transfer reagent,
- Triflation,
- Ionic mechanistic pathways
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沈阳化工大学材料科学与工程学院沈阳 110142