| Identification | Back Directory | [Name]
Perfluoro-tert-butyl phenyl sulfone | [CAS]
68596-36-1 | [Synonyms]
[[2,2,2-Trifluoro-1,1-bis(trifluoromethyl)ethyl]sulfonyl]benzene
((1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-yl)sulfonyl)benzene | [Molecular Formula]
C10H5F9O2S | [MOL File]
68596-36-1.mol | [Molecular Weight]
360.19 |
| Hazard Information | Back Directory | [Description]
The selective introduction of perfluoro-tert-butyl group (PFtB, the bulkier analogue of CF3 group)
into arenes has long been sought after but remains a formidable task. We herein report the first
general synthetic protocol to realize aromatic perfluoro-tert-butylation. The key to the success is
the identification of PFtB phenyl sulfone as a new source of PFtB anion, which reacts with arynes
in a highly regioselective manner to afford perfluoro-tert-butylated arenes in high yields. The
application of the method is demonstrated by the preparation of sensitive 19F-labeled NMR probes
with an extraordinary resolving ability.
![[[2,2,2-Trifluoro-1,1-bis(trifluoromethyl)ethyl]sulfonyl]benzene](/NewsImg/2024-01-23/6384160430010023235613227.png "[[2,2,2-Trifluoro-1,1-bis(trifluoromethyl)ethyl]sulfonyl]benzene") | [Uses]
Perfluoro-tert-butyl phenyl sulfone reacts with highly selective regio-lactones and can be used to obtain high yields of perfluoro-tert-butyl aromatics. | [References]
[1] ZHIQIANG WEI, JINBO HU*Regioselective Aromatic Perfluoro-tert-butylation Using Perfluoro-tert-butyl Phenyl Sulfone and Arynes[J]. Journal of the American Chemical Society, 2022. DOI:10.1021/jacs.2c10479. |
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