Rhodium-Catalyzed C-H Amination: A Case Study of Selectivity in C-H Functionalization Reactions

Journal Article (Journal Article)

An advanced undergraduate organic chemistry laboratory experiment involving a rhodium-catalyzed intermolecular hydrocarbon C-H oxidation reaction is described. In the initial phase of this lab, students conduct a C-H amination reaction of ethylbenzene and isolate a benzylic amine product. In the second part of the lab, competition experiments are performed to compare the relative rates of C-H insertion with electronically disparate para-substituted ethylbenzene derivatives. Reaction progress is monitored by thin-layer chromatography and the outcome quantitatively assessed using 1H NMR spectroscopy. Data from competition experiments form the basis for a discussion of reaction mechanism including analysis of putative transition structures and relative potential energy barriers for C-H oxidation. Experiments have been designed such that instructors can tailor the level of detail and discussion from introductory to advanced.

Full Text

Duke Authors

Cited Authors

  • Mack, JBC; Bedell, TA; Deluca, RJ; Hone, GAB; Roizen, JL; Cox, CT; Sorensen, EJ; Du Bois, J

Published Date

  • December 11, 2018

Published In

Volume / Issue

  • 95 / 12

Start / End Page

  • 2243 - 2248

Electronic International Standard Serial Number (EISSN)

  • 1938-1328

International Standard Serial Number (ISSN)

  • 0021-9584

Digital Object Identifier (DOI)

  • 10.1021/acs.jchemed.7b00697

Citation Source

  • Scopus