Based on Nanotechnology and Materials Science Programs, and
a Grant-in-Aid for Scientific Research from the Ministry of
Education, Culture, Science, Sports, and Technology of Japan.
We are grateful to Mr S. Kuzuya (University of Tokyo) for his
help in experiments.
Prasanth and H. Maheswaran, J. Mol. Catal. A: Chem., 2007, 268, 45–
49; M. R. Maurya, A. K. Chandrakar and S. Chand, J. Mol. Catal. A:
Chem., 2007, 274, 192–201; F. Gregori, I. Nobili, F. Bigi, R. Maggi, G.
Predieri and G. Sartori, J. Mol. Catal. A: Chem., 2008, 286, 124–127;
M. Mba, M. Pontini, S. Lovat, C. Zonta, G. Bernardinelli, P. E. Ku¨ndig
and G. Licini, Inorg. Chem., 2008, 47, 8616–8618.
12 M. K. Chaudhuri, S. K. Dehury, S. Hussain, A. Duarah, N. Gogoi and
M. L. Kantam, Adv. Synth. Catal., 2005, 347, 1349–1352.
13 A. Marques, M. di Matteo and M. -F. Ruasse, Can. J. Chem., 1998, 76,
770–775; J. Brinksma, R. La Crois, B. L. Feringa, M. I. Donnoli and
C. Rosini, Tetrahedron Lett., 2001, 42, 4049–4052; J. R. L. Smith, J.
Murray, P. H. Walton and T. R. Lowdon, Tetrahedron Lett., 2006,
47, 2005–2008; F. Hosseinpoor and H. Golchoubian, Tetrahedron
Lett., 2006, 47, 5195–5197; M. Bagherzadeh, R. Latifi, L. Tahsini and
M. Amini, Catal. Commun., 2008, 10, 196–200; M. Bagherzadeh, L.
Tahsini and R. Latifi, Catal. Commun., 2008, 9, 1600–1606.
Notes and references
1 M. C. Carren˜o, Chem. Rev., 1995, 95, 1717–1760; S. Burrage, T.
Raynham, G. Williams, J. W. Essex, C. Allen, M. Cardno, V. Swali
and M. Bradley, Chem.–Eur. J., 2000, 6, 1455–1466; C. M. Spencer and
D. Faulds, Drugs, 2000, 60, 321–329; E. N. Prilezhaeva, Russ. Chem.
Rev., 2001, 70, 897–920; S. Okabe, K. Shimosako and K. Amagase,
J. Physiol. Pharmacol., 2001, 52, 639–656; A. Padwa and M. D. Danca,
Org. Lett., 2002, 4, 715–717.
2 R. Tokuno, M. Sodeoka, K. Aoe and M. Shibasaki, Tetrahedron Lett.,
1995, 36, 8035–8038; A. Thorarensen, A. Palmgren, K. Itami and J. -E.
Ba¨ckvall, Tetrahedron Lett., 1997, 38, 8541–8544; D. G. I. Petra, P. C. J.
Kamer, A. L. Spek, H. E. Schoemaker and P. W. N. M. van Leeuwen,
J. Org. Chem., 2000, 65, 3010–3017; I. Ferna´ndez and N. Khiar, Chem.
Rev., 2003, 103, 3651–3706; R. Dorta, H. Rozenberg, L. J. W. Shimon
and S. Milstein, Chem.–Eur. J., 2003, 9, 5237–5249.
14 C. Duboc-Toia, S. Meˆnage, C. Lambeaux and M. Fontecave, Tetra-
hedron Lett., 1997, 38, 3727–3730; J. Legros and C. Bolm, Angew.
Chem., Int. Ed., 2003, 42, 5487–5489; E. Baciocchi, M. F. Gerini and A.
Lapi, J. Org. Chem., 2004, 69, 3586–3589; W. D. Kerber, B. Ramdhanie
and D. P. Goldberg, Angew. Chem., Int. Ed., 2007, 46, 3718–3721; M.
Bagherzadeh and M. Amini, Inorg. Chem. Commun., 2009, 12, 21–25.
15 S. Velusamy, A. V. Kumar, R. Saini and T. Punniyamurthy, Tetrahedron
Lett., 2005, 46, 3819–3822.
16 K. Bahrami, Tetrahedron Lett., 2006, 47, 2009–2012.
3 A. J. Mancuso and D. Swern, Synthesis, 1981, 165–185; V. Y.
Kukushkin, Coord. Chem. Rev., 1995, 139, 375–407; A. M. Khenkin
and R. Neumann, J. Am. Chem. Soc., 2002, 124, 4198–4199.
17 F. V. Tkhai, A. V. Tarakanova, O. V. Kostyuchenko, B. N. Tarasevich,
N. S. Kulikov and A. V. Anisimov, Theor. Found. Chem. Eng., 2008, 42,
636–642.
4 B. Zapata, F. Pedraza and M. A. Valenzuela, Catal. Today, 2005, 106,
219–221; E. Ito and J. A. R. van Veen, Catal. Today, 2006, 116, 446–460.
5 M. Madesclaire, Tetrahedron, 1986, 42, 5459–5495; J. -E. Ba¨ckvall, in
Modern Oxidation Methods, ed. J.-E. Ba¨ckvall, Wiley-VCH, Weinheim,
2004, pp. 193–222; P. Kowalski, K. Mitka, K. Ossowska and Z.
Kolarska, Tetrahedron, 2005, 61, 1933–1953; K. Kaczorowska, Z.
Kolarska, K. Mitka and P. Kowalski, Tetrahedron, 2005, 61, 8315–
8327.
6 A. B. E. Minidis and J. -E. Ba¨ckvall, Chem.–Eur. J., 2001, 7, 297–302;
J. H. Bing, H. X. Fang, S. D. Po and L. Zhong, Russ. J. Org. Chem.,
2006, 42, 959–961; K. R. Reddy, C. V. Rajasekhar and A. Ravindra,
Synth. Commun., 2006, 36, 3761–3766.
7 H. Firouzabadi, N. Iranpoor, A. A. Jafari and E. Riazymontazer, Adv.
Synth. Catal., 2006, 348, 434–438; M. M. Khodaei, K. Bahrami and
A. Karimi, Synthesis, 2008, 1682–1684; A. Zali, A. Shokrolahi, M. H.
Keshavarz and M. A. Zarei, Acta Chim. Slov., 2008, 55, 257–260.
8 F. van de Velde, I. W. C. E. Arends and R. A. Sheldon, J. Inorg. Biochem.,
2000, 80, 81–89.
18 W. Winter, C. Mark and V. Schurig, Inorg. Chem., 1980, 19, 2045–2048;
F. P. Ballistreri, G. A. Tomaselli and R. M. Toscano, J. Mol. Catal.,
1991, 68, 269–275; M. Bonchio, T. Carofiglio, F. Di Furia and R.
Fornasier, J. Org. Chem., 1995, 60, 5986–5988; K. -H. Ahn, S. Choi, H.
-J. Nam and S. -H. Byeon, Bull. Korean Chem. Soc., 2004, 25, 341–342;
K. Jeyakumar and D. K. Chand, Tetrahedron Lett., 2006, 47, 4573–
4576; C. A. Gamelas, T. Lourenc¸o, A. P. da Costa, A. L. Simpl´ıcio, B.
Royo and C. C. Roma˜o, Tetrahedron Lett., 2008, 49, 4708–4712; M.
Bagherzadeh, L. Tahsini, R. Latifi, A. Ellern and L. K. Woo, Inorg.
Chim. Acta, 2008, 361, 2019–2024.
19 T. Soundiressane, S. Selvakumar, S. Me´nage, O. Hamelin, M. Fontecave
and A. P. Singh, J. Mol. Catal. A: Chem., 2007, 270, 132–143; O.
Hamelin, S. Me´nage, F. Charnay, M. Chavarot, J. -L. Pierre, J. Pe´caut
and M. Fontecave, Inorg. Chem., 2008, 47, 6413–6420; S. Calmettes,
B. Albela, O. Hamelin, S. Me´nage, F. Miomandre and L. Bonneviot,
New J. Chem., 2008, 32, 727–737.
20 V. Cimpeanu, V. Paˆrvulescu, V. I. Paˆrvulescu, J. M. Thompson and C.
Hardacre, Catal. Today, 2006, 117, 126–132.
9 M. Matteucci, G. Bhalay and M. Bradley, Org. Lett., 2003, 5, 235–237.
10 Y. Watanabe, T. Numata and S. Oae, Synthesis, 1981, 204–206; R. S.
Reddy, J. S. Reddy, R. Kumar and P. Kumar, J. Chem. Soc., Chem.
Commun., 1992, 84–85; A. Corma, M. Iglesias and F. Sa´nchez, Catal.
Lett., 1996, 39, 153–156; V. Hulea, P. Moreau and F. D. Renzo,
J. Mol. Catal. A: Chem., 1996, 111, 325–332; N. N. Trukhan, V. N.
Romannikov, A. N. Shmakov, M. P. Vanina, E. A. Paukshtis, V. I.
Bukhtiyarov, V. V. Kriventsov, I. Y. Danilov and O. A. Kholdeeva,
Microporous Mesoporous Mater., 2003, 59, 73–84; O. A. Kholdeeva,
M. S. Mel’gunov, A. N. Shmakov, N. N. Trukhan, V. V. Kriventsov,
V. I. Zaikovskii, M. E. Malyshev and V. N. Romannikov, Catal. Today,
2004, 91–92, 205–209; V. Cimpeanu, V. I. Parvulescu, P. Amoro´s, D.
Beltra´n, J. M. Thompson and C. Hardacre, Chem.–Eur. J., 2004, 10,
4640–4646; C. V. Reddy and J. G. Verkade, J. Mol. Catal. A: Chem.,
2007, 272, 233–240; M. Mba, L. J. Prins and G. Licini, Org. Lett.,
2007, 9, 21–24; W. Al-Maksoud, S. Daniele and A. B. Sorokin, Green
Chem., 2008, 10, 447–451; A. M. Cojocariu, P. H. Mutin, E. Dumitriu,
F. Fajula, A. Vioux and V. Hulea, Chem. Commun., 2008, 5357–5359.
11 A. V. Ramaswamy, S. Sivasanker and P. Ratnasamy, Microporous
Mater., 1994, 2, 451–458; C. Bolm and F. Bienewald, Angew. Chem.,
Int. Ed. Engl., 1996, 34, 2640–2642; T. P. Tang, S. K. Volkman and
J. A. Ellman, J. Org. Chem., 2001, 66, 8772–8778; A. V. Anisimov, E. V.
Fedorova, A. Z. Lesnugin, V. M. Senyavin, L. A. Aslanov, V. B. Rybakov
and A. V. Tarakanova, Catal. Today, 2003, 78, 319–325; P. Plitt, H.
Pritzkow and R. Kra¨mer, Dalton Trans., 2004, 2314–2320; R. Trivedi
and P. Lalitha, Synth. Commun., 2006, 36, 3777–3782; M. R. Maurya,
A. Kumar, M. Ebel and D. Rehder, Inorg. Chem., 2006, 45, 5924–5937;
X. -Y. Yi, G. K. Y. Ng, I. D. Williams and W. -H. Leung, Inorg. Chim.
Acta, 2006, 359, 3581–3588; M. Al-Hashimi, E. Fisset, A. C. Sullivan
and J. R. H. Wilson, Tetrahedron Lett., 2006, 47, 8017–8019; K. L.
21 H. S. Schultz, H. B. Freyermuth and S. R. Buc, J. Org. Chem., 1963, 28,
1140–1142; A. Arcoria, F. P. Ballistreri, G. A. Tomaselli, F. Di Furia
and G. Modena, J. Mol. Catal., 1984, 24, 189–196; N. M. Gresley,
W. P. Griffith, A. C. Laemmel, H. I. S. Nogueira and B. C. Parkin,
J. Mol. Catal. A: Chem., 1997, 117, 185–198; F. M. Collins, A. R. Lucy
and C. Sharp, J. Mol. Catal. A: Chem., 1997, 117, 397–403; B. M.
Choudary, B. Bharathi, C. V. Reddy and M. L. Kantam, J. Chem. Soc.,
Perkin Trans. 1, 2002, 2069–2074; Y. M. A. Yamada, H. Tabata, H.
Takahashi and S. Ikegami, Synlett, 2002, 0231–2034; V. V. Thakur and
A. Sudalai, Tetrahedron: Asymmetry, 2003, 14, 407–410; B. Karimi,
M. Ghoreishi-Nezhad and J. H. Clark, Org. Lett., 2005, 7, 625–628;
D. H. Koo, M. Kim and S. Chang, Org. Lett., 2005, 7, 5015–5018; V.
Hulea, A. -L. Maciuca, F. Fajula and E. Dumitriu, Appl. Catal., A,
2006, 313, 200–207; S. Nlate, L. Plault and D. Astruc, New J. Chem.,
2007, 31, 1264–1274; B. Sreedhar, P. Radhika, B. Neelima, N. Hebalkar
and A. K. Mishra, Catal. Commun., 2008, 10, 39–44; X. Ying and W.
Jun-Fa, J. Mol. Catal. A: Chem., 2008, 280, 142–147.
22 W. Adam, C. M. Mitchell and C. R. Saha-Mo¨ller, Tetrahedron, 1994,
50, 13121–13124; S. Yamazaki, Bull. Chem. Soc. Jpn., 1996, 69, 2955–
2959; C. C. Roma˜o, F. E. Khu¨n and W. A. Herrmann, Chem. Rev., 1997,
97, 3197–3246; H. Q. N. Gunaratne, M. A. McKervey, S. Feutren,
J. Finlay and J. Boyd, Tetrahedron Lett., 1998, 39, 5655–5658; J. H.
Espenson, Chem. Commun., 1999, 479–488; R. Bernini, E. Mincione,
M. Barontini, F. Crisante, G. Fabrizi and A. Gambacorta, Tetrahedron,
2007, 63, 6895–6900.
23 A. Scarso and G. Strukul, Adv. Synth. Catal., 2005, 347, 1227–1234;
P. Sgarbossa, E. Pizzo, A. Scarso, S. M. Sbovata, R. A. Michelin, M.
Mozzon, G. Strukul and F. Benetollo, J. Organomet. Chem., 2006, 691,
3659–3666.
5516 | Dalton Trans., 2010, 39, 5509–5518
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