Homogeneous catalytic hydrogenation of perfluoro methyl esters

The first example of perfluoroalkyl methyl ester RfC(O)OMe (Rf = C3F7, C5F11) reduction by homogeneous catalytic hydrogenation with the ruthenium catalyst Ru-MACHO™ is herein reported. The hydrogenation process leads to the corresponding perfluorinated alcohols thus replacing sodium borohydride that has so far represented the state of art in perfluoro ester reduction.

[1]  D. Spasyuk,et al.  Replacing phosphorus with sulfur for the efficient hydrogenation of esters. , 2013, Angewandte Chemie.

[2]  Zheng Wang,et al.  Catalytic hydrogenation of cyclic carbonates: a practical approach from CO2 and epoxides to methanol and diols. , 2012, Angewandte Chemie.

[3]  J. Vincent Recent advances of fluorous chemistry in material sciences. , 2012, Chemical communications.

[4]  D. Spasyuk,et al.  From esters to alcohols and back with ruthenium and osmium catalysts. , 2012, Angewandte Chemie.

[5]  Takao Saito,et al.  Catalytic Hydrogenation of Esters. Development of an Efficient Catalyst and Processes for Synthesising (R)-1,2-Propanediol and 2-(l-Menthoxy)ethanol , 2012 .

[6]  P. Metrangolo,et al.  The fluorous effect in biomolecular applications. , 2012, Chemical Society reviews.

[7]  P. Metrangolo,et al.  Organic fluorine compounds: a great opportunity for enhanced materials properties. , 2011, Chemical Society reviews.

[8]  A. Slawin,et al.  Hydrogenation of Aldehydes, Esters, Imines, and Ketones Catalyzed by a Ruthenium Complex of a Chiral Tridentate Ligand , 2007 .

[9]  Ashwin Rao,et al.  Synthesis, characterization, and interfacial properties of an oligomeric, cationic fluorooxetane. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[10]  Richard J Farn Chemistry and technology of surfactants , 2006 .

[11]  W. R. Dolbier,et al.  Fluorine chemistry at the millennium , 2005 .

[12]  G. Gambaretto,et al.  Electrochemical fluorination: state of the art and future tendences , 2004 .

[13]  Bruce E. Smart,et al.  Fluorine Compounds, Organic , 2000 .

[14]  S. Yano,et al.  A fatal case of acute boric acid poisoning. , 1993, Journal of toxicology. Clinical toxicology.

[15]  M. E. Mortensen,et al.  Fatal ingestion of boric acid in an adult. , 1992, The American journal of emergency medicine.

[16]  J. H. Simons,et al.  The Electrochemical Process for the Production of Fluorocarbons , 1949 .