Hypervalent Iodine Reagents Enable Metal-Free Amination of Arylboronic Acids
1-Amino-1,2-benziodoxol-3(1H)-one [A3839] is a hypervalent iodine reagent used for the electrophilic amination of aromatic boronic acids. The reaction proceeds without any metal catalyst, which is its key advantage, and it is applicable to (hetero)aryl boronic acids bearing both electron-donating and electron-withdrawing groups. In the reported example, A3839 aminates o-tolylboronic acid to give a p-toluidine derivative (R=H) in 84% yield.¹) TCI also demonstrated the amination of 4-(methoxycarbonyl)phenylboronic acid, which gave methyl 4-aminobenzoate in 87% yield using cesium carbonate in THF at 50 °C for two days.¹) Its companion reagent, 1-Acetoxy-1,2-benziodoxol-3(1H)-one [A3838], enables the synthesis of reagents that introduce a desired primary amine.¹) Because A3839 may be explosive in contact with metals, avoid metal contact during handling.
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References
- Amino‐λ3‐iodane‐Enabled Electrophilic Amination of Arylboronic Acid Derivatives. K. Kiyokawa, K. Kawanaka, S. Minakata, Angew. Chem. Int. Ed. 2024, 63, e202319048. doi:10.1002/anie.202319048
Source
- TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20260427
- TCI product page A3839: tcichemicals.com/ID/en/p/A3839
- TCI brochure RR220: Hypervalent Iodine Reagents for Electrophilic Amination of Aromatic Boronic Acids
For research and laboratory use only, not for human consumption.
