Deuteration of Arenes via Pd-Catalyzed C-H Activation: A Lesson in Nondirected C-H Activation, Isotopic Labeling, and NMR Characterization.
| Autor: | Deufel F; Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany., van Gemmeren M; Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany. |
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| Jazyk: | angličtina |
| Zdroj: | Journal of chemical education [J Chem Educ] 2024 Jul 16; Vol. 101 (8), pp. 3410-3417. Date of Electronic Publication: 2024 Jul 16 (Print Publication: 2024). |
| DOI: | 10.1021/acs.jchemed.4c00270 |
| Abstrakt: | Isotopic labeling is an important tool in medicinal research, metabolomics, and for understanding reaction mechanisms. In this context, transition metal-catalyzed C-H activation has emerged as a key technology for deuterium incorporation via hydrogen isotope exchange. A detailed and easy-to-implement experimental procedure for a nondirected arene deuteration has been developed that exclusively uses commercial equipment and chemicals. The protocol is ideally suited for students and other prospective applicants who are not experts in catalysis. The degree of deuterium incorporation was analyzed via different means like mass spectrometry and 1 H and 2 H nuclear magnetic resonance (NMR). A hands-on understanding of quantitative NMR, as well as the influence of H/D exchange on experimental spectra, was conveyed by comparative NMR spin simulations. Students were measurably familiarized with the concepts of C-H activation, isotope effects, and basics in experimental catalysis. Competing Interests: The authors declare no competing financial interest. (© 2024 The Authors. Published by American Chemical Society and Division of Chemical Education, Inc.) |
| Databáze: | MEDLINE |
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