Salen-Mn(III)-complex-catalyzed oxidations of secondary alcohols
Wei Sun
State Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, China
Search for more papers by this authorChun-Gu Xia
State Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, China
Search for more papers by this authorWei Sun
State Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, China
Search for more papers by this authorChun-Gu Xia
State Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, China
Search for more papers by this authorAbstract
Secondary alcohols were catalytically oxidized with diacetoxyiodobenzene as oxidant in the presence of salen-Mn(III) complex to afford the corresponding ketones, in up to 99% yield, using CH2Cl2 or water as reaction media.
References
- 1
Ley, S. V;
Madin, A.
In, Comprehensive Organic Synthesis,
Vol. 7,
Eds.: B. M. Trost;
I. Fleming,
Pergamon, Oxford,
1991,
p. 305.
10.1016/B978-0-08-052349-1.00192-X Google Scholar
- 2(a)
Poos, G. I;
Arth, G. E;
Beyler, R. E;
Sarett, L. H.,
J. Am. Chem. Soc.
1953,
75,
422.
(b)
Collins, J. C;
Hess, W. W;
Frank, F. J.,
Tetrahedron Lett.
1968,
9,
3363.
10.1016/S0040-4039(00)89494-0 Google Scholar(c) Corey, E. J; Suggs, J. W., Tetrahedron Lett. 1975, 16, 1641. (d) Corey, E. J; Schmidt, G., Tetrahedron Lett. 1979, 19, 399.10.1016/S0040-4039(01)93515-4 Google Scholar(e) Lou, J. D; Xu, Z. N., Tetrahedron Lett. 2002, 43, 6095. (f) Lou, J. D; Xu, Z. N., Tetrahedron Lett. 2002, 43, 6149.
- 3(a) Markó, I. E; Giles, P. R; Tsukazaki, M; Chellé-Regnaut, I; Urch, C; Brown, S. M., J. Am. Chem. Soc. 1997, 119, 12661. (b) Markó, I. E; Giles, P. R; Tsukazaki, M; Brown, S. M; Urch, C. J., Science 1996, 2044. (c) Yamaguchi, K; Mori, K; Mizugaki, T; Ebitani, K; Kaneda, K., J. Am. Chem. Soc. 2000, 122, 7144. (d) Miyata, A; Murakami, M; Irie, R; Katsuki, T., Tetrahedron Lett. 2001, 42, 7067. (e) Muldoon, J; Brown, S. N., Org. Lett. 2002, 4, 1043.
- 4(a) Fey, T; Fisher, H; Bachmann, S; Albert, K; Bolm, C., J. Org. Chem. 2001, 66, 8154 and references cited therein. (b) Luca, L. D; Giacomelli, G; Porcheddu, A., Org. Lett. 2001, 3, 3041. (c) Ansari, I. A; Gree, R., Org. Lett. 2002, 4, 1507 and references cited therein.
- 5 Iwasa, S; Morita, K; Tajima, K; Fakhruddin, A; Nishiyama, H., Chem. Lett. 2002, 284.
- 6(a)
Katsuki, T.,
Coord. Chem. Rev.
1995,
140,
189.
(b)
Katsuki, T.,
J. Mol. Catal., A
1996,
113.
87.
(c)
Ito, Y. N;
Katsuki, T.,
Bull. Chem. Soc. Jpn.
1999,
72,
603.
(d)
Jacobsen, E. N;
Wu, M. H.
in, Comprehensive Asymmetric Catalysis,
Vol. 2,
Eds.: E. N. Jacobsen;
A. Pfaltz;
H. Yamamoto,
Springer, Berlin,
1999,
p. 649.
10.1007/978-3-642-58571-5 Google Scholar(e) Masutani, K; Uchida, T; Irie, R; Katsuki, T., Tetrahedron Lett. 2000, 41, 5119. (f) Aikawa, K; Irie, R; Katsuki, T., Tetrahedron 2001, 57, 845. (g) Kohmura, Y; Katsuki, T., Tetrahedron Lett. 2001, 42, 3339. (h) Saito, B; Katsuki, T., Tetrahedron Lett. 2001, 42, 3873. (i) Ohta, C; Katsuki, T., Tetrahedron Lett. 2001, 42, 3885.
- 7 Adam, W; Hajra, S; Herderich, M; Saha-Möller, C. R., Org. Lett. 2000, 2, 2773.
- 8(a) Lindström, U. M., Chem. Rev. 2002, 102, 2751. (b) Li, C. J. In, Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Eds.: P. T. Anastas; T. C. Williamson, Oxford, New York, 1998, p. 234.
- 9 Sun, W; Wang, H. W; Xia, C. G; Li, J. W; Zhao, P. Q., Angew. Chem., Int. Ed. 2003, 42, 1042.
- 10 Larrow, J. F; Jacobsen, E. N., J. Org. Chem. 1994, 59, 1539.
