Kessler, Simon N. and Neuburger, Markus and Wegner, Hermann A.. (2012) Domino Inverse Electron-Demand Diels-Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid. Journal of the American Chemical Society, 134 (43). pp. 17885-17888.
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Official URL: https://edoc.unibas.ch/94294/
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Abstract
A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.
| Faculties and Departments: | 05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Synthese (Wegner) |
|---|---|
| UniBasel Contributors: | Wegner, Hermann A. A. |
| Item Type: | Article, refereed |
| Article Subtype: | Research Article |
| Publisher: | American Chemical Society |
| ISSN: | 0002-7863 |
| e-ISSN: | 1520-5126 |
| Note: | Publication type according to Uni Basel Research Database: Journal article |
| Identification Number: |
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| Last Modified: | 19 Apr 2023 06:17 |
| Deposited On: | 19 Apr 2023 06:17 |
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