M. R. Axet, S. Castillón, C. Claver, K. Philippot, P. Lecante, B. Chaudret
FULL PAPER
Karmazin-Brelot, A. Neels, T. Bürgi, R. G. Finke, C. M.
Hagen, Organometallics 2005, 24, 6104–6119.
catalytic tests. After cooling, the reaction mixture was analyzed by
gas chromatography. The aldehydes resulting from hydrofor-
mylation were oxidized into carboxylic acids to determine the enan-
tiomeric excess (ee) by gas chromatography.
[4]
[5]
T. Pery, K. Pelzer, G. Buntkowski, K. Philippot, H.-H. Lim-
bach, B. Chaudret, ChemPhysChem 2005, 6, 605–607.
J. García-Antón, M. R. Axet, S. Jansat, K. Philippot, B. Chau-
dret, T. Pery, G. Buntkowsky, H.-H. Limbach, Angew. Chem.
Int. Ed. 2008, 47, 2074–2078.
a) K. Philippot, B. Chaudret, CR. Chim. 2003, 6, 1019–1034;
b) B. Chaudret, C.R. Phys. 2005, 6, 117–131; c) B. Chaudret, in
Topics in Organometallic Chemistry Vol. 16: Surface and Inter-
facial Organometallic Chemistry and Catalysis, Springer, Berlin,
2005, pp. 233–259.
a) A. Roucoux, in Topics in Organometallic Chemistry Vol. 16:
Surface and Interfacial Organometallic Chemistry and Catalysis,
Springer, Berlin, 2005, pp. 261–279; b) S. Jansat, D. Picurelli,
K. Pelzer, K. Philippot, M. Gómez, G. Muller, P. Lecante, B.
Chaudret, New J. Chem. 2006, 30, 115–122.
a) T. W. Smith (Xerox Corporation), US 4252678, 1981; b) F.
Wen, H. Boënnemann, J. Jiang, D. Lu, Y. Wang, Z. Jin, Appl.
Organomet. Chem. 2005, 19, 81–89; c) L. Tuchbreiter, S. Meck-
ing, Macromol. Chem. Phys. 2007, 208, 1688–1693; d) D. Han,
X. Li, H. Zhang, Z. Liu, J. Li, C. Li, J. Catal. 2006, 243, 318–
328; e) A. J. Bruss, M. A. Gelesky, G. Machado, J. Dupont, J.
Mol. Catal. A 2006, 252, 212–218.
a) M. D. Fryzuk, W. E. Piers in Organometallic Syntheses (Eds.:
R. B. King, J. J. Eisch), Elsevier, Amsterdam, 1986, vol. 3, p.
128; b) W. A. Herrmann in Synthetic Methods of Organometal-
lic and Inorganic Chemistry (Ed.: W. A. Herrmann), Thieme,
Stuttgart, 1996, p. 38.
R. Uson, L. A. Oro, J. A. Cabeza, Inorg. Synth. 1985, 23, 126.
G. J. H. Buisman, M. E. Martin, E. J. Vos, A. Klootwijk,
P. C. J. Kamer, P. W. N. M. van Leeuwen, Tetrahedron: Asym-
metry 1995, 6, 719–738.
In Situ HP NMR Hydroformylation Experiments: A sapphire tube
(ø10 mm) was filled under an argon atmosphere with Rh3 (10 mg)
nanoparticles and ligand 1 (19.3ϫ10–3 mmol) in [D8]toluene
(2 mL). The HP NMR tube was purged three times with CO and
pressurized to the appropriate pressure of CO/H2 mixture. After a
reaction time of 45 h, during which the solution was shaken at
70 °C, the solution was analyzed.
[6]
[7]
[8]
Acknowledgments
We are grateful to the Spanish Ministerio de Educacion y Ciencia
(CTQ2007-62288/BQU, Consolider Ingenio 2010, CSD2006-0003)
and the Generalitat de Catalunya (2005SGR007777 Distinction for
Research Promotion, 2003, C .C.) for financial support. The au-
thors also thank the Departament d’Universitats, Recerca i Societat
de la Informació i del Fons Social Europeu for an FPI grant
(M. R. A.). K. P. and B. C. thank the TEMSCAN (Service Com-
mun de Microscopie Electronique de l’Université Paul Sabatier) for
TEM analysis, Egide (PAI 07165RE) and CNRS (PICS 2428,
Picasso 04230PL) for financial support.
[9]
[1] a) A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 2002, 102,
3757–3778; b) A. Roucoux, K. Philippot, “Hydrogenation with
Noble Metal Nanoparticles” in Handbook of Homogeneous
Hydrogenations (Ed.: G. de Vries), Wiley-VCH, Weinheim,
2007, pp. 217–256; c) M. T. Reetz, R. Breinbauer, K. Wan-
ninger, Tetrahedron Lett. 1996, 37, 4499–4502; d) M. T. Reetz,
E. Westermann, Angew. Chem. Int. Ed. 2000, 39, 165–168; e)
M. Moreno-Mañas, R. Pleixats, S. Villarroya, Organometallics
2001, 20, 4524–4528; f) C. Rocaboy, J. A. Gladysz, Org. Lett.
2002, 4, 1993–1996; g) C. C. Cassol, A. P. Umpierre, G. Mach-
ado, S. I. Wolke, J. Dupont, J. Am. Chem. Soc. 2005, 127, 3298–
3299; h) D. Astruc, F. Lu, J. Ruiz Aranzaes, Angew. Chem. Int.
Ed. 2005, 44, 7852–7872; i) J. G. de Vries, Dalton Trans. 2006,
421–429; j) J. A. Widegren, R. G. Finke, J. Mol. Catal. A 2003,
191, 187–207.
[2] a) M. Beller, H. Fischer, K. Kuehlein, C.-P. Reisinger, W. A.
Herrmann, J. Organomet. Chem. 1996, 520, 257–259; b) M. T.
Reetz, G. Lohmer, Chem. Commun. 1996, 1921; c) S. Kling-
elhöfer, W. Heitz, A. Greiner, S. Oestreich, S. Foerster, M. An-
tonietti, J. Am. Chem. Soc. 1997, 119, 10116–10120; d) J.
Le Bars, U. Specht, J. S. Bradley, D. G. Blackmond, Langmuir
1999, 15, 7621–7625; e) L. K. Yeung, R. M. Crooks, Nano Lett.
2001, 1, 14–17; f) Y. Li, E. Boone, M. A. El-Sayed, Langmuir
2002, 18, 4921–4925; g) R. Narayanan, M. A. El-Sayed, J. Am.
Chem. Soc. 2003, 125, 8340–8347; h) S. Jansat, M. Gomez, K.
Philippot, G. Muller, E. Guiu, C. Claver, S. Castillón, B. Chau-
dret, J. Am. Chem. Soc. 2004, 126, 1592–1593; i) I. Favier, M.
Gómez, G. Muller, M. R. Axet, S. Castillón, C. Claver, S. Jan-
sat, B. Chaudret, K. Philippot, Adv. Synth. Catal. 2007, 349,
2459–2469.
[10]
[11]
[12]
[13]
[14]
M. R. Axet, J. Benet-Buchholz, C. Claver, S. Castillón, Adv.
Synth. Catal. 2007, 349, 1983–1998.
T. D. Ewers, A. K. Sra, B. C. Norris, R. E. Cable, C.-H. Cheng,
D. F. Shantz, R. E. Schaak, Chem. Mater. 2005, 17, 514–520.
a) O. Vidoni, K. Philippot, C. Amiens, B. Chaudret, O. Balmes,
J. Malm, J. Bovin, F. Senocq, M. J. Casanove, Angew. Chem.
Int. Ed. 1999, 38, 3736–3738; b) K. Pelzer, O. Vidoni, K. Phil-
ippot, B. Chaudret, V. Collière, Adv. Funct. Mater. 2003, 13,
118–126.
T. Ould Ely, C. Amiens, B. Chaudret, E. Snoeck, M. Verelst,
M. Respaud, J.-M. Broto, Chem. Mater. 1999, 11, 526–529.
a) H. P. Liang, H. M. Zhang, J. S. Hu, Y. G. Guo, L. J. Wan,
C. L. Bai, Angew. Chem. Int. Ed. 2004, 43, 1540–1543; b) G.
Schmid, A. Lehnert, J. Malm, J. Bovin, Angew. Chem. Int. Ed.
Engl. 1991, 30, 874–876; c) Y. J. Song, Y. Yang, C. J. Medforth,
E. Pereira, A. K. Singh, H. F. Xu, Y. B. Jiang, C. J. Brinker, F.
van Swol, J. A. Shelnutt, J. Am. Chem. Soc. 2004, 126, 635–
645.
O. Pámies, G. Net, A. Ruiz, C. Claver, Tetrahedron: Asymmetry
2000, 11, 1097–1108.
P. W. N. M. van Leeuwen, C. Claver (Eds.), Rhodium Catalyzed
Hydroformylation, Kluwer Academic, Dordrecht, 2000, vol.
22..
Q. Wang, H. Liu, M. Han, X. Li, D. Jiang, J. Mol. Catal. A
1997, l18, 145.
A. Gual, M. R. Axet, K. Philippot, B. Chaudret, A. Denicourt-
Nowicki, A. Roucoux, S. Castillón, C. Claver, Chem. Commun.,
DOI:10.1039/B802316F.
[15]
[16]
[17]
[18]
[19]
[20]
[3] a) I. W. Davies, L. Matty, D. L. Hughes, P. Reider, J. Am.
Chem. Soc. 2001, 123, 10139–10140; b) J. A. Widegren, R. G.
Finke, J. Mol. Catal. A 2003, 198, 317–341; c) C. M. Hagen,
L. Vieille-Petit, G. Laurenczy, G. Süss-Fink, R. G. Finke, Orga-
nometallics 2005, 24, 1819–1831; d) L. Vieille-Petit, G. Süss-
Fink, B. Therrien, T. R. Ward, H. Stoeckli-Evans, G. Labat, L.
Received: April 24, 2008
Published Online: July 7, 2008
3466
www.eurjic.org
© 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Inorg. Chem. 2008, 3460–3466