Chen, Kang and Berg, Nele and Gschwind, Ruth and Koenig, Burkhard (2017) Selective Single C(sp(3))-F Bond Cleavage in Trifluoromethylarenes: Merging Visible-Light Catalysis with Lewis Acid Activation. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 139 (51). pp. 18444-18447. ISSN 0002-7863,
Full text not available from this repository. (Request a copy)Abstract
The conversion of easily available trifluoromethylarenes into aryldifluoromethyl compounds, which are valuable motifs in the pharmaceutical chemistry, is highly atom-and step-economical. However, the single C(sp(3))-F bond cleavage of ArCF3 is a great challenge because of the chemical inertness of the C(sp(3))-F bond and the difficult selectivity control of monodefluorination. We report here the first example of single C(sp(3))-F functionalization of trifluoromethylarenes via visible-light catalysis merged with Lewis acid activation. The method allows good chemoselectivity control and shows good functional group tolerance. Mechanistic studies suggest an in situ-generated borenium cationic species as the key intermediate for C(sp(3))-F bond cleavage in this reaction.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-F BOND; ELECTRON-TRANSFER REACTIONS; FACILE ACCESS; MEDICINAL CHEMISTRY; HYDRODEFLUORINATION; FLUORINE; FUNCTIONALIZATION; ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE; DERIVATIVES; ALKYLATION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:18 |
| Last Modified: | 20 Feb 2019 11:07 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1668 |
Actions (login required)
 |
View Item |
