Selective CH Functionalization of Methane, Ethane, and Propane by a Perfluoroarene Iodine(III) Complex

Michael M. Konnick, Brian G. Hashiguchi, Deepa Devarajan, Nicholas C. Boaz, T. Brent Gunnoe, John Taylor Groves, Niles Gunsalus, Daniel H. Ess, Roy A. Periana

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Abstract

Direct partial oxidation of methane, ethane, and propane to their respective trifluoroacetate esters is achieved by a homogeneous hypervalent iodine(III) complex in non-superacidic (trifluoroacetic acid) solvent. The reaction is highly selective for ester formation (>99 %). In the case of ethane, greater than 0.5 M EtTFA can be achieved. Preliminary kinetic analysis and density functional calculations support a nonradical electrophilic CH activation and iodine alkyl functionalization mechanism. Gas up: Direct partial oxidation of methane, ethane, and propane to their respective trifluoroacetate (TFA) esters is achieved by a homogeneous hypervalent iodine(III) complex in non-superacidic solvent (HTFA). The reaction is highly selective, and for ethane, greater than 0.5 M Et=TFA can be achieved. Preliminary kinetic analysis and density functional calculations support a nonradical electrophilic CH activation and iodine alkyl functionalization mechanism.

Original languageEnglish (US)
Pages (from-to)10490-10494
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number39
DOIs
StatePublished - Jul 14 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • C=H activation
  • alkanes
  • hypervalent compounds
  • iodine
  • main-group elements

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    Konnick, M. M., Hashiguchi, B. G., Devarajan, D., Boaz, N. C., Gunnoe, T. B., Groves, J. T., Gunsalus, N., Ess, D. H., & Periana, R. A. (2014). Selective CH Functionalization of Methane, Ethane, and Propane by a Perfluoroarene Iodine(III) Complex. Angewandte Chemie - International Edition, 53(39), 10490-10494. https://doi.org/10.1002/anie.201406185