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 T Groves; Niles Gunsalus; Daniel H Ess; Roy A Periana

doi:10.1002/anie.201406185

Selective CH functionalization of methane, ethane, and propane by a perfluoroarene iodine(III) complex

Angew Chem Int Ed Engl. 2014 Sep 22;53(39):10490-4. doi: 10.1002/anie.201406185. Epub 2014 Aug 11.

Authors

Michael M Konnick¹, Brian G Hashiguchi, Deepa Devarajan, Nicholas C Boaz, T Brent Gunnoe, John T Groves, Niles Gunsalus, Daniel H Ess, Roy A Periana

Affiliation

¹ The Scripps Energy & Materials Center, Department of Chemistry, The Scripps Research Institute, Jupiter, FL 33458 (USA). mkonnick@scripps.edu.

PMID: 25131994
DOI: 10.1002/anie.201406185

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.

Keywords: CH activation; alkanes; hypervalent compounds; iodine; main-group elements.