diffraction studies were obtained from slow diffusion of diethyl
ether into an acetonitrile solution. Data reduction was performed
9 (a) C. J. Mathews, P. J. Smith and T. Welton, Chem. Commun.,
000, 1249; (b) F. Fernandez, B. Cordero, J. Durand, G. Muller,
F. Malbosc, Y. Kihn, E. Teuma and M. Gomez, Dalton Trans.,
007, 5572; (c) J. Duranda, E. Teumaa, F. Malboscb, Y. Kihnc and
2
´
3
using CrysAlis RED, and structure solution and refinement
9
´
2
4
0
were carried out using the SHELX97 software package. The
structure was solved by Patterson methods and successive
interpretation of the difference Fourier maps, followed by full
´
`
M. Gomez, Catal. Commun., 2008, 9, 273; (d) V. Calo, A. Nacci,
A. Monopoli and F. Montingelli, J. Org. Chem., 2005, 70, 6040.
0 B. F. G. Johnson, Top. Catal., 2003, 24, 147.
1
1
1
1 N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.
2 J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508.
2
matrix least-squares refinement (against F ). All non-hydrogen
atoms were refined anisotropically, and the contribution of the
hydrogen atoms, in their calculated positions, was included in
the refinement using a riding model. Relevant crystallographic
data are compiled in Table 5.
13 (a) G. P. Wolfe, R. A. Singer, B. H. Yang and S. L. Buchwald,
J. Am. Chem. Soc., 1999, 121, 9550; (b) G. Matsuo and
S. Matsumura, Tetrahedron Lett., 2001, 42, 7375; (c) A. H.
M. de Vries and J. G. de Vries, Adv. Synth. Catal., 2004, 346, 1812.
1
1
1
1
1
4 C. Chiappe, D. Pieraccini, D. Zhao, Z. Fei and P. J. Dyson, Adv.
Synth. Catal., 2006, 348, 68.
5 D. Zhao, Z. Fei, R. Scopelliti and P. J. Dyson, Inorg. Chem., 2004,
43, 2197.
6 S. R. Dubbaka, D. Zhao, Z. Fei, C. M. Rao Volla, P. J. Dyson and
P. Vogel, Synlett, 2006, 3155.
7 X. Yang, Z. Fei, D. Zhao, W. H. Ang, Y. Li and P. J. Dyson,
Inorg. Chem., 2008, 47, 3292.
Acknowledgements
We thank the EPFL and the Swiss National Science Foundation
for financial support. Y.L. thanks the Natural Science
Foundation of China (contract 20425619) and the Program
for Changjiang Scholars and Innovative Research Teams in
Universities (under file number IRT 0641). We also thank
8 F. Mazille, Z. Fei, D. Kuang, D. Zhao, S. M. Zakeeruddin,
M. Graetzel and P. J. Dyson, Inorg. Chem., 2006, 45, 1585.
19 P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, Wiley-
VCH, Weinheim, 2003.
0 C. J. Mathews, P. J. Smith, T. Welton, A. J. P. White and
Prof. Philippe-Andre Buffat at the Center Interdisciplinaire de
´
2
Microscopie Electronique (CIME) at the EPFL for help with
the TEM.
D. J. Williams, Organometallics, 2001, 20, 3848.
21 J. McNulty, A. Capretta, J. Wilson, J. Dyck, G. Adjabeng and
A. Robertson, Chem. Commun., 2002, 1986.
2 M. Lombardo, M. Chiarucci and C. Trombini, Green Chem., 2009,
1, 574.
3 G. Zou, Z. Wang, J. Zhu, J. Tang and M. Y. He, J. Mol. Catal. A:
Chem., 2003, 206, 193.
24 X. Yang, Z. Fei, T. J. Geldbach, A. D. Phillips, C. G. Hartinger,
Y. Li and P. J. Dyson, Organometallics, 2008, 27, 3971.
25 C. Chiappe, Monatsh. Chem., 2007, 138, 1035.
26 C. F. Poole, J. Chromatogr., A, 2004, 1037, 49.
27 C. C. Cassol, A. P. Umpierre, G. Machado, S. I. Wolke and
J. Dupont, J. Am. Chem. Soc., 2005, 127, 3298.
28 (a) C. W. Scheeren, G. Machado, J. Dupont, P. F. P. Fichtner and
S. R. Texeira, Inorg. Chem., 2003, 42, 4738; (b) J. Dupont,
G. S. Fonseca, A. P. Umpierre, P. F. P. Fichtner and
S. R. Teixeira, J. Am. Chem. Soc., 2002, 124, 4228.
29 V. Calo, A. Nacci, A. Monopoli, S. Laera and N. Cioffi, J. Org.
Chem., 2003, 68, 2929.
30 X.-D. Mu, D. G. Evans and Y. Kou, Catal. Lett., 2004, 97, 151.
2
2
1
References
1
(a) K. R. Seddon, J. Chem. Technol. Biotechnol., 1997, 68, 351;
b) T. Welton, Chem. Rev., 1999, 99, 2071; (c) P. Wasserscheid and
(
W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772; (d) P. J. Dyson,
Appl. Organomet. Chem., 2002, 16, 495; (e) J. Dupont, R. F.
D. Souza and P. A. Z. Suarez, Chem. Rev., 2002, 102, 3667;
(f) C. Ciappe and D. Pieraccini, J. Phys. Org. Chem., 2005, 18,
275; (g) P. Migowski and J. Dupont, Chem.–Eur. J., 2007, 13, 32.
A. E. Visser, R. P. Swatloski, W. M. Reichert, R. Mayton, S. Sheff,
A. Wierzbicki, J. H. Davis, Jr. and R. D. Rogers, Chem. Commun.,
2
2001, 135.
J. H. Davis, Jr., Chem. Lett., 2004, 33, 1072.
Z. Fei, T. J. Geldbach, D. Zhao and P. J. Dyson, Chem.–Eur. J.,
3
4
2006, 12, 2122.
(a) H. Xue, B. Twamley and J. M. Shreeve, J. Org. Chem., 2004,
5
6
9, 1397; (b) B. A. Omotowa and J. M. Shreeve, Organometallics,
31 J. Durand, E. Teuma, F. Malbosc, Y. Kihn and M. Go
Commun., 2008, 9, 273.
´
mez, Catal.
2004, 23, 783; (c) B. A. Omotowa, B. S. Phillips, J. S. Zabinski and
J. M. Shreeve, Inorg. Chem., 2004, 43, 5466; (d) O. D. Gupta,
P. D. Armstrong and J. M. Shreeve, Tetrahedron Lett., 2003, 44,
32 R. R. Deshmukh, R. Rajagopal and K. V. Srinivasan, Chem.
Commun., 2001, 1544.
9
367; (e) Y. Gao, S. W. Arritt, B. Twamley and J. M. Shreeve,
33 D.-J. Guo and H.-L. Li, J. Colloid Interface Sci., 2005, 286, 274.
34 Z. Fei, D. Zhao, D. Pieraccini, W. H. Ang, T. J. Geldbach,
R. Scopelliti, C. Chiappe and P. J. Dyson, Organometallics,
2007, 26, 1588.
35 Y. Umebayashi, S. Fukuda, Y. Kameda and S. Kohara, Research
Frontiers, 2007, 118.
36 R. Bini, O. Bortolini, C. Chiappe, D. Pieraccini and T. Siciliano,
J. Phys. Chem. B, 2007, 111, 598.
37 (a) M. T. Barros, C. D. Maycock, M. I. Madureira and
M. R. Ventura, Chem. Commun., 2001, 1662; (b) V. Farina and
E. Napolitano, Organometallics, 2003, 22, 4030.
Inorg. Chem., 2005, 44, 1704; (f) J.-C. Xiao, C. Ye and
J. M. Shreeve, Org. Lett., 2005, 7, 1963.
D. Zhao, Z. Fei, T. J. Geldbach, R. Scopelliti and P. J. Dyson,
J. Am. Chem. Soc., 2004, 126, 15876.
(a) J. Ropponen, M. Lahtinen, S. Busi, M. Nissinen,
E. Kolehmainen and K. Rissanen, New J. Chem., 2004, 28, 1426;
(b) B. Martiz, R. Keyrouz, S. Gmouh, M. Vaultier and V. Jouikov,
Chem. Commun., 2004, 674.
For example see: (a) C. Daguenet and P. J. Dyson, Organometallics,
6
7
8
2004, 23, 6080; (b) P. Illner, A. Zahl, R. Puchta, H. N. van Eikema,
P. Wasserscheid and R. van Eldik, J. Organomet. Chem., 2005, 690,
38 P. J. Dyson and J. S. McIndoe, Inorg. Chim. Acta, 2003, 354, 68.
39 Oxford Diffraction Ltd., M.P., Abingdon OX14 4 RX, UK, 2007.
40 G. M. Sheldrick, SHELX-97, Structure Solution and Refinement
Package, Universitaet Goettingen, Goettingen, Germany, 1997.
3
567; (c) C. Daguenet and P. J. Dyson, Organometallics, 2006, 25,
811; (d) P. Illner, S. Begel, S. Kern, R. Puchta and R. van Eldik,
5
Inorg. Chem., 2009, 48, 588.
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