Table 2 Hydrogenation reactions in [bmim]PF6 using PdOAc,N as
catalyst
2
3
4
5
6
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´
nin and J. Muzart, Tetrahe-
´
nin and J. Muzart,
Run Substrate
17
Time/h Products
20
% Yield
97
´
(a) J. J. Berzelius, Ann. Physik. Chem. Poggendorf, 1828, 13, 435–
488; (b) J. Muzart, Tetrahedron, 2003, 59, 5789–5816.
(a) R. McCrindle, G. Ferguson, G. J. Arsenault and A. J. Mc
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R. McCrindle, G. Ferguson, G. J. Arsenault, A. J. McAlees and
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18
19
22
20
98
82
17
92
7
8
´
de Reims Champagne-
20
40
9
(a) H. Bonnemann, W. Brijoux, R. Brinkmann, E. Dinjus, T.
¨
Joussen and B. Korall, Angew. Chem., Int. Ed. Engl., 1991, 30,
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1994, 116, 7401–7402; (c) M. T. Reetz, W. Helbig, S. A. Quaiser,
U. Stimming, N. Breuer and R. Vogel, Science, 1995, 267, 367–
Table 3 Hydrogenation reactions with different substrates carried out
a
with recycled [bmim]PF6 and PdOAc,N
369; (d) Z. Kiraly, B. Veisz, A. Mastalir, Z. Razga and I. Dekany,
´
Cycle Substrate
1
Time/h Products
20
% Yield
97
Chem. Commun., 1999, 1925–1926; (e) S. Mukhopadhyay, G.
Rothenberg, D. Gitis and D. Sasson, J. Org. Chem., 2000, 65,
3107–3109; (f) M. T. Reetz, M. Winter, R. Breinbauer, T.
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10 (a) N. A. Dhas and A. Gedanken, J. Mater. Chem., 1998, 8, 445–
450; (b) M. T. Reetz and M. Maase, Adv. Mater., 1999, 11, 773–
777; (c) M. T. Reetz and E. Westermann, Angew. Chem., Int. Ed.,
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and J. G. Vries, Chem. Commun., 2004, 1559–1563.
11 (a) B. Yoon, H. Kim and C. M. Wai, Chem. Commun., 2003,
1040–1041; (b) J. Huang, T. Jiang, B. Han, H. Gao, Y. Chang,
G. Zhao and W. Wu, Chem. Commun., 2003, 1654–1655; (c)
S. Kidambi, J. Dai, J. Li and M. L. Bruening, J. Am. Chem.
Soc., 2004, 126, 2658–2659; (d) J. Huang, T. Jiang, B. Han, Z. Liu,
W. Wu, Y. Chang and G. Zhao, Angew. Chem., Int. Ed., 2004, 43,
2
3
23
21
97
81
18
9
4
120
20
1397–1399; (e) K. Anderson, S. C. Fernandez, C. Hardacre and
´
90
90
P. C. Marr, Inorg. Chem. Commun., 2004, 7, 73–76.
12 (a) H. Kanno and K. Osanai, Tetrahedron Lett., 1995, 36, 5375–
5378; (b) H. Sajiki and K. Hirota, Tetrahedron, 1998, 54, 13981–
13996; (c) H. Sajiki, Tetrahedron Lett., 1995, 36, 3465–3468; (d)
H. Sajiki, K. Hattori and K. Hirota, J. Org. Chem., 1998, 63,
7990–7992.
5
13 (a) A. Rutar, F. Tratar and D. Kikelj, Synthesis, 1995, 512–514;
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14 (a) D. Dubreuil, J. Cleophax, M. Vieira de Almeida, C. Verre-
´
Sebrie, J. Liaigre, G. Vass and S. D. Gero, Tetrahedron, 1997, 53,
a
Reactions carried out at room temperature using a balloon filled with
hydrogen, 0.01 equiv. of catalyst, 2 ml of [bmim]PF6 for 1 mmol
of substrate.
16747–16766; (b) S. Maki, M. Okawa, T. Makii, T. Hirano and
H. Niwa, Tetrahedron Lett., 2003, 44, 3717–3721.
15 Electronic diffraction showed the characteristic pattern of Pd0
species: face-centred cube with average d-spacing values of 2.246,
1.938 and 1.358 A (see Electronic supplementary information).
16 S. Maki, M. Okawa, R. Matsui, T. Hirano and H. Niwa, Synlett.,
2001, 1590–1592.
References
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N e w J . C h e m . , 2 0 0 4 , 2 8 , 1 5 5 0 – 1 5 5 3
1553