Iron-catalyzed ligand-free diazidation of alkenes controlled by the ratio of TBHP to TMSN <sub>3</sub>

The diazidation of alkenes through an iron-catalyzed, ligand-free system has been established, providing straightforward access to structurally vicinal diazides in good yields at room temperature with TMSN<sub>3</sub> as the azido source. The ratio of <sup><i>t</i></sup>BuOOH to TMSN<sub>3</sub> was essential for the reaction: one equivalent TMSN<sub>3</sub> was needed to react with <sup><i>t</i></sup>BuOOH to form HN<sub>3</sub> as a nucleophile in the reaction ultimately achieving the diazidation of alkenes.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-11-13
DOI
https://doi.org/10.1039/d4ob01698j
Citations
1
Primary Topic
Synthesis and Catalytic Reactions
Type
article
Field-Weighted Citation Impact
0.25

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Iron-catalyzed ligand-free diazidation of alkenes controlled by the ratio of TBHP to TMSN 3

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article

Iron-catalyzed ligand-free diazidation of alkenes controlled by the ratio of TBHP to TMSN 3

G. ZHANG, Xinyue Li, Min Jiang, Xingyu Li, Fang Fang, Shu Tang, Qian He, Hongzhou Yu
article en
1 citations

Abstract

The diazidation of alkenes through an iron-catalyzed, ligand-free system has been established, providing straightforward access to structurally vicinal diazides in good yields at room temperature with TMSN<sub>3</sub> as the azido source. The ratio of <sup><i>t</i></sup>BuOOH to TMSN<sub>3</sub> was essential for the reaction: one equivalent TMSN<sub>3</sub> was needed to react with <sup><i>t</i></sup>BuOOH to form HN<sub>3</sub> as a nucleophile in the reaction ultimately achieving the diazidation of alkenes.

Organic & Biomolecular ChemistryVol. 23(2)
Anhui University of Traditional Chinese Medicine (CN)
Anhui University of Chinese Medicine
Clean water and sanitation
Openalex Percentile: Top 46%
Synthesis and Catalytic Reactions
0.25
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