RSC Advances
Communication
1967, 1, 77; (c) G. Siegemund, W. Schwertfeger, A. Feiring,
B. Smart, F. Behr, H. Vogel and B. McKusick, Fluorine
Compounds, Organic in Ullmann’s Encyclopedia of Industrial
Chemistry, Wiley-VCH, Weinheim, 2005; (d) F. G. Drakesmith,
Electrofluorination of Organic Compounds, Topics in Current
Chemistry, Springer, Berlin-Heidelberg, 1997, vol. 193; (e) J.
H. Simons, J. Electrochem. Soc., 1949, 95, 47; (f) L. Conte and G.
P. Gambaretto, J. Fluorine Chem., 2004, 125, 139.
5 (a) W. V. Childs, Phillips Petroleum Company, US 4,156,791,
1979; (b) S. A. Fontana, C. A. P. Tonelli and P. Gavezotti, Solvay
Specialty Polymers Italy S.p.A., WO 2012168156, 2012; (c) R.
D. Chambers, Fluorine in Organic Chemistry, Blackwell
Publishing, 2004.
6 (a) European Chemicals Bureau; IUCLID Dataset, Boric acid
(10043-35-3) (2000 CD-ROM edition). Available from: http://
esis.jrc.ec.europa.eu/; (b) Y. Ishii, N. Fujizuka, T. Takahashi,
K. Shimizu, A. Tuchida, S. Yano, T. Naruse and T. Chishiro, Clin.
Toxicol., 1993, 31, 345; (c) A. Restuccio, M. E. Mortensen and M.
T. Kelley, Am. J. Emerg. Med., 1992, 10, 545.
7 In August 2008, the EU decided to amend its classification as
reprotoxic category 2 and to apply the risk phrases R60 (may
impair fertility) and R61 (may cause harm to the unborn child).
8 (a) M. L. Clarke, M. B. Diaz-Valenzuela and A. M. Z. Slawin,
Organometallics, 2007, 26, 16; (b) A. Ishii, T. Ootsuka,
M. Imamura, T. Nishimiya and K. Kimura, WO 2013018573,
2013, in Japanese; (c) A. Ishii, T. Ootsuka, T. Ishimaru and
M. Imamura, WO 2012105431, 2012, in Japanese.
In conclusion, in this communication we have shown that the
ruthenium catalyst Ru-MACHO is an active catalyst for the
hydrogenation of perfluorinated methyl esters under very mild
conditions and represents a valid alternative to the use of metal
hydrides.
M.C.C. wishes to thank the University of Bologna and the
`
Ministero dell’Universita e della Ricerca (MUR) (project: ‘‘New
strategies for the control of reactions: interactions of molecular
fragments with metallic sites in unconventional species’’, PRIN
2007) for financial support.
Notes and references
§ Under the following conditions: 10% Ru on Carbon with hydrogen
pressures up to 50 bar and temperature up to 120 uC a 1% conversion (GC)
was observed.
1 (a) P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis,
Reactivity, Applications, Wiley-VCH, Verlag, 2nd edn, 2013; (b)
R. Berger, G. Resnati, P. Metrangolo, E. Weber and J. Hulliger,
Chem. Soc. Rev., 2011, 40, 3496; (c) W. R. Dolbier Jr., J. Fluorine
Chem., 2005, 126, 157; (d) M. Cametti, B. Crousse, P. Metrangolo,
R. Milani and G. Resnati, Chem. Soc. Rev., 2012, 41, 31; (e) J.-
M. Vincent, Chem. Commun., 2012, 48, 11382.
2 (a) S. Schellenberger, J. Pahnke, R. Friedrich and G. Jonschker,
Europ. Coat. Jnl., 2012, 11, 32; (b) R. J. Farn, Chemistry and
Technology of Surfactants, Blackwell Publishing, 2006, pp. 228–
229; (c) A. Rao, Y. Kim, C. M. Kausch, V. M. Russell and R.
R. Thomas, Langmuir, 2006, 22, 4811.
ic-investors.com/) an industrial group composed of 19
chemical companies, operating worldwide in base chemicals,
fine chemicals and polymers.
9 (a) W. Kuriyama, T. Matsumoto, Y. Ino, O. Ogata and N. Saeki,
Takasago Int. Co., WO 2011048727, 2011; (b) W. Kuriyama,
T. Matsumoto, O. Ogata, Y. Ino, K. Aoki, S. Tanaka, K. Ishida,
T. Kobayashi, N. Sayo and T. Saito, Org. Process Res. Dev., 2012,
16, 166; (c) D. Spasyuk, S. Smith and D. G. Gusev, Angew. Chem.,
Int. Ed., 2012, 51, 2772; (d) Z. Han, L. Rong, J. Wu, L. Zhang,
Z. Wang and K. Ding, Angew. Chem., Int. Ed., 2012, 51, 13041; (e)
D. Spasyuk, S. Smith and d. G. Gusev, Angew. Chem., Int. Ed.,
2013, 52, 2538.
4 (a) J. H. Simons, Fluorine Chemistry, ed. J. H. Simons, Academic
Press, New York, 1950, vol. 1; (b) S. Nagase, Fluorine Chem. Rev.,
This journal is ß The Royal Society of Chemistry 2013
RSC Adv.