Andries-Ulmer, Anna and Brunner, Christoph and Rehbein, Julia and Gulder, Tanja (2018) Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 140 (40). pp. 13034-13041. ISSN 0002-7863,
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Despite ample evidence for the unique reactivity offered by hypervalent F-iodanes, mechanistic investigations fall far behind. In order to shed light on the unusual behavior of such F-reagents, we conducted computational and experimental studies on the chemodivergent transformation of styrenes. We identified the spirocyclic F-cyclopropane as the common intermediate for both the C,H-fluorination and C,H-amination pathways. The fate of this key compound is determined by the extent of cationic charge delocalization controlled by the N-substituents. Exploiting this phenomenon, a multitude of different transformations have become available, leading, i.e., to the regiodivergent synthesis of indoles and tryptophans.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HYPERVALENT IODINE REAGENTS; ATOM-TRANSFER REACTIONS; METAL-FREE SYNTHESIS; FLUOROIODANE REAGENT; GEMINAL DIFLUORINATION; MEDICINAL CHEMISTRY; ALKENES; ACID; OLEFINS; TRIFLUOROMETHYLATION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Dec 2019 13:13 |
| Last Modified: | 05 Dec 2019 13:13 |
| URI: | https://pred.uni-regensburg.de/id/eprint/13701 |
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