5 (a) G.-J. ten Brink, I. W. C. E. Arends and R. A. Sheldon, Science,
2000, 287, 1636; (b) R. A. Sheldon, I. W. C. E. Arends, G.-J. ten Brink
and A. Dijksman, Acc. Chem. Res., 2002, 35, 774.
6 B. P. Buffin, J. P. Clarkson, N. L. Belitz and A. Kundu, J. Mol. Catal.
A: Chem., 2005, 225, 111.
7 F. A. Cotton, M. Matusz and B. Zhong, Inorg. Chem., 1988, 27, 4368.
8 M. McCann and A. Carvill, Polyhedron, 1993, 12, 1163.
9 F. A. Cotton, L. Labella and M. Shang, Inorg. Chem., 1992, 31, 2385.
10 F. A. Cotton, T. Datta, L. Labella and M. Shang, Inorg. Chim. Acta,
1993, 203, 55.
11 Characterization data of 3: IR (KBr) 1635 (CLO), 1578 (O–C–O, sym.),
1444 (O–C–O, asym.) cm21. UV-vis (H2O) lmax (log e): 424 (2.78) nm.
1H NMR (D2O) d 243.5 (br, cis-O2CCH3, 6H), 241.7 (br, trans-
O2CCH3, 3H). 13C NMR (D2O) d 2143.6 (trans-O2CCH3), 2138.6 (cis-
O2CCH3). Anal. Calcd for C7H9O9Ru2?H2O: C, 18.39; H, 2.42%.
Found: C, 18.64; H, 2.54%.
Notes and references
1 (a) Multiphase Homogeneous Catalysis, ed. B. Cornils, W. A. Herrmann,
I. T. Horva´th, W. Leither, S. Mecking, H. Oliver-Bourbigou and
D. Vogt, Wiley-VCH, Weinheim, 2005; (b) Aqueous-Phase
Organometallic Catalysis, ed. B. Cornils and W. A. Herrmann, Wiley-
VCH, Weinheim, 1998; (c) Organic Synthesis in Water, ed. P. A. Grieco,
Blackie Academic & Professional, London, 1998.
2 (a) I. W. C. E. Arends and R. A. Sheldon, in Modern Oxidation
Methods, ed. J.-E. Ba¨ckvall, Wiley-VCH, Weinheim, 2004, pp. 83–118;
(b) B.-Z. Zhan and A. Thompson, Tetrahedron, 2004, 60, 2917; (c)
D. Lenoir, Angew. Chem., Int. Ed., 2006, 45, 3206; (d) I. E. Marko´,
P. R. Giles, M. Tsukazaki, I. Chelle´-Regnaut, C. J. Urch and
S. M. Brown, J. Am. Chem. Soc., 1997, 119, 12661; (e) M. Lee and
S. Chang, Tetrahedron Lett., 2000, 41, 7507; (f) A. Dijksman,
A. Marino-Gonza´lez, A. M. I. Payeras, I. W. C. E. Arends and
R. A. Sheldon, J. Am. Chem. Soc., 2001, 123, 6826; (g) G. Csjernyik,
12 The carbonate-bridged structure of 3 was determined based on the
=
similar complex: Ru2(O2CC10H15)3(CO3)(MeOH)2 (O2CC10H15
1-adamantanecarboxylate): F. A. Cotton, L. Labella and M. Shang,
Inorg. Chim. Acta, 1992, 197, 149.
´
A. H. Ell, L. Fadini, B. Pugin and J.-E. Ba¨ckvall, J. Org. Chem., 2002,
67, 1657; (h) T. Nishimura, T. Onoue, K. Ohe and S. Uemura,
J. Org. Chem., 1999, 64, 6750; (i) K. P. Peterson and R. C. Larock,
J. Org. Chem., 1998, 63, 3185; (j) D. R. Jensen, M. J. Schultz,
J. A. Mueller and M. S. Sigman, Angew. Chem., Int. Ed., 2003,
42, 3810.
3 For reviews on heterogeneous oxidations of alcohols, see: (a) T. Mallat
and A. Baiker, Chem. Rev., 2004, 104, 3037; (b) M. Besson and
P. Gallezot, Catal. Today, 2000, 57, 127.
4 Recent green methods: (a) Y. Uozumi and R. Nakao, Angew.
Chem., Int. Ed., 2003, 42, 194; (b) K. Mori, T. Hara,
T. Mizugaki, K. Ebitani and K. Kaneda, J. Am. Chem. Soc., 2004,
126, 10657.
13 K. D. Drysdale, E. J. Beck, T. S. Cameron, K. N. Robertson and
M. A. S. Aquino, Inorg. Chim. Acta, 1997, 256, 243.
14 A typical procedure for the aerobic oxidation of 1: a mixture of 1
(122 mg, 1.0 mmol) and 3 (22.9 mg, 0.05 mmol) in water (1.5 mL) and
toluene (0.5 mL) was stirred at 80 uC for 36 h under an O2 atmosphere
(1 atm, O2 balloon). After extraction with toluene and filtration through
a pad of silica gel, ketone 2 (114 mg, 95%) was obtained in a pure form
(GLC yield, 99%).
15 (a) H. Tomioka, K. Takai, K. Oshima and H. Nozaki, Tetrahedron
Lett., 1981, 22, 1605; (b) S.-I. Murahashi, T. Naota, K. Ito, Y. Maeda
and H. Taki, J. Org. Chem., 1987, 52, 4319.
This journal is ß The Royal Society of Chemistry 2006
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