We have developed an advanced undergraduate organic chemistry laboratory experiment that exposes students to C–H oxidation catalysis. In the initial phase of this lab, students conduct a rhodium-catalyzed C–H amination reaction of ethylbenzene and isolate a benzylic sulfonamide product. In the second part of the lab, competition experiments are performed to compare the relative rates of C–H insertion with electronically disparate <i>para</i>-substituted ethylbenzene derivatives. Reaction progress is monitored by thin-layer chromatography and the outcome quantitatively assessed using <sup>1</sup>H NMR spectroscopy. In the final segment of the lab, data from the competition experiments are combined to generate a Hammett plot, which forms the basis for a discussion of reaction mechanism, putative transition structures, relative potential energy barriers, and product selectivity in C–H oxidation reactions. These experiments have been designed such that instructors can tailor the level of detail and discussion from introductory to advanced.

Rhodium-catalyzed C–H amination: Case study of selectivity in C–H functionalization reactions

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.