Bidentate lewis acid catalysis for organic synthesis

Published on June 15, 2015

New concepts in catalysis are without doubt the key for the success of efficient and sustainable synthesis and will be the basis to address today’s challenges of our society, such as energy and shortage of resources. In this video the basic idea of using bidentate Lewis acids in organic synthesis is explained, which has been developed in the group of H. Wegner at the Justus Liebig University in Giessen (Germany). Finally, the methodology is showcased by demonstrating an inverse electron-demand Diels-Alder reaction in the laboratory.

Related Video:
Recipe for the preparation of a bidentate Lewis acid catalyst

Wegner Group | Justus Liebig University Giessen, Germany

Hermann Wegner studied chemistry in Göttingen, Boston, Stanford and Oxford. After completion of his habilitation at the University of Basel he moved to his current position as a Professor for Organic Chemistry at the Justus Liebig University Giessen. His research interests are in Lewis acid catalysis, molecular switches and novel aromatics for functional materials.

Luca Schweighauser joined the group of Hermann Wegner as a PhD student in 2011. His studies are focused on Lewis acid catalysis and azobenzene based molecular switches.

Sources

Kessler, S. N., Wegner, H. A.: “Lewis Acid Catalyzed Inverse Electron-Demand Diels-Alder Reaction of 1,2-Diazines” Org. Lett. 2010, 12 (18), 4062-4065, DOI: 10.1021/ol101701z.

Kessler, S. N., Neuburger, M., Wegner, H. A.: “Bidentate Lewis Acids for the Activation of 1,2-Diazines – A New Mode of Catalysis.” Eur. J. Org. Chem. 2011, 17, 3238–3245, DOI: 10.1002/ejoc.201100335.

Kessler, S. N., Wegner, H. A.: “One-Pot Synthesis of Phthalazines and Pyridazino-aromatics: A Novel Strategy for Substituted Naphthalenes” Org. Lett. 2012, 14 (13), 3268–3271, DOI: 10.1021/ol301167q.

Kessler, S. N., Neuburger, M., Wegner, H. A.: “Domino Inverse Electron-Demand Diels–Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid.” J. Am. Chem. Soc. 2012, 134 (43), 17885–17888, DOI: 10.1021/ja308858y.

Lu, Z., Hausmann, H., Becker, S., Wegner, H. A.: “Aromaticity as Stabilizing Element in the Bidentate Activation for the Catalytic Reduction of Carbon Dioxide” J. Am. Chem. Soc. 2015, 137 (16), 5332–5335, DOI: 10.1021/jacs.5b02905.

Schweighauser, L., Bodoky, I., Kessler, S. N., Häussinger, D., Wegner, H. A.: “Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels–Alder Reaction for the Selective Functionalization of Aldehydes.” Synthesis 2012, 44 (14), 2195-2199, DOI: 10.1055/s-0031-1291127.

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