Wu, Guojiao and Jacobi von Wangelin, Axel (2018) Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes. CHEMICAL SCIENCE, 9 (7). pp. 1795-1802. ISSN 2041-6520, 2041-6539
Full text not available from this repository. (Request a copy)Abstract
Stereoselective additions of highly functionalized reagents to available unsaturated hydrocarbons are an attractive synthetic tool due to their high atom economy, modularity, and rapid generation of complexity. We report efficient cobalt-catalyzed (E)-halofluoroalkylations of alkynes/alkenes that enable the construction of densely functionalized, stereodefined fluorinated hydrocarbons. The mild conditions (2 mol% cat., 20 degrees C, acetone/water, 3 h) tolerate various functional groups, i.e. halides, alcohols, aldehydes, nitriles, esters, and heteroarenes. This reaction is the first example of a highly stereoselective cobalt-catalyzed halo-fluoroalkylation. Unlike related cobalt-catalyzed reductive couplings and Heck-type reactions, it operates via a radical chain mechanism involving terminal halogen atom transfer which obviates the need for a stoichiometric sacrificial reductant.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CROSS-COUPLING REACTIONS; VITREOUS CARBON CATHODES; ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS; COPPER-MEDIATED DIFLUOROMETHYLATION; PERFLUOROALKYL IODIDES; GRIGNARD-REAGENTS; RADICAL-ADDITION; ROOM-TEMPERATURE; TRIFLUOROMETHYLTHIOLATION REACTIONS; FLUOROALKYL IODIDES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Axel Jacobi von Wangelin |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 19 Mar 2020 11:17 |
| Last Modified: | 19 Mar 2020 11:17 |
| URI: | https://pred.uni-regensburg.de/id/eprint/15028 |
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