We thank Villum Fonden (T.P.P.) and the SFB 749 (DFG) for support and financial contributions to this project. TMP=2,2,6,6-tetramethylpiperidyl.
Continuous Flow Magnesiation of Functionalized Heterocycles and Acrylates with TMPMgCl⋅LiCl†
Article first published online: 24 JUN 2014
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 30, pages 7933–7937, July 21, 2014
How to Cite
Petersen, T. P., Becker, M. R. and Knochel, P. (2014), Continuous Flow Magnesiation of Functionalized Heterocycles and Acrylates with TMPMgCl⋅LiCl. Angew. Chem. Int. Ed., 53: 7933–7937. doi: 10.1002/anie.201404221
- Issue published online: 18 JUL 2014
- Article first published online: 24 JUN 2014
- Manuscript Received: 11 APR 2014
- flow chemistry;
A flow procedure for the metalation of functionalized heterocycles (pyridines, pyrimidines, thiophenes, and thiazoles) and various acrylates using the strong, non-nucleophilic base TMPMgCl⋅LiCl is reported. The flow conditions allow the magnesiations to be performed under more convenient conditions than the comparable batch reactions, which often require cryogenic temperatures and long reaction times. Moreover, the flow reactions are directly scalable without further optimization. Metalation under flow conditions also allows magnesiations that did not produce the desired products under batch conditions, such as the magnesiation of sensitive acrylic derivatives. The magnesiated species are subsequently quenched with various electrophiles, thereby introducing a broad range of functionalities.