Hypervalent Iodine Reagent for Fluorinations and Balz–Schiemann Catalysis
1-Fluoro-3,3-dimethyl-1,2-benziodoxole (F0957) is a hypervalent iodine compound that is stable to moisture and air and is useful for fluorinations. It can be applied to alpha-fluorinations of 1,3-dicarbonyl compounds, 1,1-difluorinations of styrene derivatives, and fluorinative intramolecular cyclizations.¹) ²) ³) F0957 also serves as a catalyst for Balz–Schiemann reactions. In the presence of a catalytic amount of F0957 and BF3·OEt2, aryl diazonium tetrafluoroborate salts react at room temperature to 60 °C to afford the corresponding fluorinated aryl products in good yields. This reaction proceeds at a lower temperature than the conventional Balz–Schiemann reaction and is applicable to various compounds bearing electron-withdrawing groups such as esters, as well as heteroarenes. It is anticipated that this chemistry will be used in process chemistry and late-stage fluorination of pharmaceuticals and materials.
Related products
- TCI F0957 1391728-13-4 1-Fluoro-3,3-dimethyl-1,2-benziodoxole
- TCI S0446 14104-20-2 Silver Tetrafluoroborate
References
- Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride. G. C. Geary, E. G. Hope, K. Singh, A. M. Stuart, Chem. Comm. 2013, 49, 9263. doi:10.1039/C3CC44792H
- Mild Silver‐Mediated Geminal Difluorination of Styrenes Using an Air‐ and Moisture‐Stable Fluoroiodane Reagent. N. A. Ilchenko, B. O. A. Tasch, K. J. Szabó, Angew. Chem. Int. Ed. 2014, 53, 12897. doi:10.1002/anie.201408812
- Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent. W. Yuan, K. J. Szabó, Angew. Chem. Int. Ed. 2015, 54, 8533. doi:10.1002/anie.201503373
Download TCI brochure Unique Fluorinating Reagent with Various Reactivities (PDF)
Source
- TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20181203
- TCI product page F0957: tcichemicals.com/ID/en/p/F0957
- TCI brochure RR056: Unique Fluorinating Reagent with Various Reactivities
For research and laboratory use only, not for human consumption.
