small amount of catalyst, and could eliminate the use of a large
amounts of bromine used in the present route of vitamin D3 and
overcome the drawbacks of the known oxidation methods.
Further research in cooperative catalysis with Co(OAc)2 and
Mn(OAc)2 should lead to a universal method for the effective
usage of NHPI. Our research in this field and in other aerobic
oxidations for the vitamin industry are in progress.33–36
15 T. K. M. Shing, Y. Y. Ying and L. S. Pak, Org. Lett., 2006, 8, 3149.
16 S. K. Klitgaard, K. Egeblad, U. V. Mentzel, A. G. Popov, T. Jensen,
E. Taarning, I. S. Nielsen and C. H. Christensen, Green Chem., 2008,
10, 419.
17 J. L. G. Ruano, A. Parra and J. Aleman, Green Chem., 2008, 10, 706.
18 F. Li, J. Chen, Q. H. Zhang and Y. Wang, Green Chem., 2008, 10,
553.
19 S. Yamamoto, S. Sakaguchi and Y. Ishii, Green Chem., 2003, 5, 300.
20 Y. Ishii, S. Sakaguchi and T. Iwahama, Adv. Synth. Catal., 2001, 343,
393.
21 C. Gambarotti, C. Punta, F. Recupero, Encyclopedia of Reagents for
Organic SynthesisJohn Wiley & Sons: Weinheim, 2005.
22 F. Minisci, F. Recupero, G. F. Pedulli and M. Lucarini, J. Mol. Catal.
A: Chem., 2003, 204–205, 63.
Acknowledgements
We thank the support of the National Natural Science Founda-
tion of China (no. 20773109 and 20803062).
23 F. Minisci, C. Punta and F. Recupero, J. Mol. Catal. A: Chem., 2006,
251, 129.
24 R. A. Sheldon and I. W. C. E. Arends, Adv. Synth. Catal., 2004, 346,
1051.
References
25 A. Karakurt, S. Dalkara, M. Ozalp, S. Ozbey, E. Kendi and J. P.
Stables, Eur. J. Med. Chem., 2001, 36, 421.
26 F. Joseph, F. Claude, P. Karlheinzdr, EP Pat., 0 198 351, 1986.
27 F. Joseph, F. Claude, P. Karlheinzdr, US Pat., 5 030 739, 1991.
28 G. Y. Yang, Y. F. Ma and J. Xu, J. Am. Chem. Soc., 2004, 126, 10542.
29 C. Einhorn, J. Einhorn, C. Marcadal and J. L. Pierre, Chem.
Commun., 1997, 447.
1 E. C. McLaughlin, H. Choi, K. Wang, G. Chiou and M. P. Doyle,
J. Org. Chem., 2009, 74, 730.
2 J. A. R. Salvador and J. H. Clark, Green Chem., 2002, 4, 352.
3 K. P. Cheng, H. Nagana, L. Bang and G. Ourisson, J. Chem. Res.
(S), 1977, 217.
4 R. P. Heaney, Clin. J. Am. Soc. Nephrol., 2008, 3, 1535.
5 M. P. Rappoldt, L. F. Pauli, J. Hoogendoorn, US Pat., 4 464 298,
1984.
30 Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama and
Y. Nishiyama, J. Org. Chem., 1995, 60, 3934.
31 Y. Danhong, L. Mingdeng, Z. Wenjun and G. Lin, Catal. Commun.,
2008, 9, 2407.
32 P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. C. Tsang, Green
Chem., 2004, 6, 310.
33 J. Y. Mao, N. Li, H. R. Li and X. B. Hu, J. Mol. Catal. A: Chem.,
2006, 258, 178.
34 J. Y. Mao, X. B. Hu, H. R. Li, Y. Sun, C. M. Wang and Z. Chen,
Green Chem., 2008, 10, 827.
35 W. H. Guan, C. M. Wang, X. Yun, X. B. Hu, Y. Wang and H. R. Li,
Catal. Commun., 2008, 9, 1979.
36 C. M. Wang, W. H. Guan, P. H. Xie, X. Yun, H. R. Li, X. B. Hu and
Y. Wa n g , Catal. Commun., 2009, 10, 725.
6 M. Jansen, US Pat., 6 180 805, 2001.
7 C. Hojae and P. D. Michael, Org. Lett., 2007, 9, 5349.
8 T. W. Tan, L. Zhang, CN Pat., 101 220 075, 2008.
9 W. G. Salmond, M. A. Barta and J. L. Havens, J. Org. Chem., 1978,
43, 2057.
10 M. A. Fousteris, A. I. Koutsourea, S. S. Nikolaropoulos, A. Riahi
and J. Muzart, J. Mol. Catal. A: Chem., 2006, 250, 70.
11 A. J. Pearson and G. R. Han, J. Org. Chem., 1985, 50, 2791.
12 J. A. R. Salvador and S. M. Silvestre, Tetrahedron, 2007, 63, 2439.
13 P. Marwah, A. Marwah and H. A. Lardy, Green Chem., 2004, 6, 570.
14 E. S. Arsenou, A. I. Koutsourea, M. A. Fousteris and S. S.
Nikolaropoulos, Steroids, 2003, 68, 407.
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