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Selective CH Functionalization of Methane, Ethane, and Propane by a Perfluoroarene Iodine(III) Complex
Author(s) -
Konnick Michael M.,
Hashiguchi Brian G.,
Devarajan Deepa,
Boaz Nicholas C.,
Gunnoe T. Brent,
Groves John T.,
Gunsalus Niles,
Ess Daniel H.,
Periana Roy A.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406185
Subject(s) - hypervalent molecule , chemistry , electrophile , propane , trifluoroacetic acid , surface modification , methane , iodine , solvent , alkyl , alkene , organic chemistry , photochemistry , catalysis
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.