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

James B.C. Mack, T. Aaron Bedell, Ryan J. Deluca, Graham A.B. Hone, Jennifer L. Roizen, Charles T. Cox, Erik J. Sorensen, J. Du Bois

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1 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2243-2248
Number of pages6
JournalJournal of Chemical Education
Volume95
Issue number12
DOIs
StatePublished - Dec 11 2018

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Education

Keywords

  • Catalysis
  • Hands-On Learning/Manipulatives
  • Kinetics
  • Laboratory Instruction
  • Metals
  • NMR Spectroscopy
  • Organic Chemistry
  • Oxidation/Reduction
  • Synthesis
  • Upper-Division Undergraduate

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