Room-temperature Swern oxidations by using a microscale flow system

Angewandte Chemie - International Edition

Volumn 44, Issue 16, 2005, Pages 2413-2416

  Kawaguchi, Tatsuya ^a   Miyata, Hiroyuki ^b   Ataka, Kikuo ^b   Mae, Kazuhiro ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b UBE INDUSTRIES LTD   (Japan)

Author keywords

Alcohols; Microreactors; Oxidation; Swern oxidation; Synthetic methods

Indexed keywords

ALCOHOLS; CHEMICAL REACTORS; HIGH TEMPERATURE EFFECTS; MIXERS (MACHINERY);

MICROMIXERS; MICROSCALE FLOW SYSTEM; ROOM TEMPERATURE (RT); SWERN OXIDATION;

OXIDATION;

EID: 18044395547     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462466     Document Type: Article

References (40)

1. a) Microreaction Technology (Ed.: W. Ehrfeld), Springer, Berlin, 1998;
2. b) W. Ehrfeld, V. Hessel, H. Löwe, Microreactors, Wiley-VCH, Weinheim, 2000;
3. c) Microsystem Technology in Chemistry and Life Sciences (Eds.: A. Manz, H. Becker), Springer, Berlin. 1999;
4. d) V. Hessel, S. Hardt, H. Löwe, Chemical Micro Process Engineering, Wiley-VCH, Weinheim, 2004.
5. a) H. Salimi-Moosavi, T. Tang, D. J. Harrison, J. Am. Chem. Soc. 1997, 119, 8716-8717;
6. b) C. de Bellefon, N. Tanchoux, S. Caravieilhes, P. Grenouillet, V. Hessel, Angew. Chem. 2000, 112, 3584-3587; Angew. Chem. Int. Ed. 2000, 39, 3442-3445;
7. b) C. de Bellefon, N. Tanchoux, S. Caravieilhes, P. Grenouillet, V. Hessel, Angew. Chem. 2000, 112, 3584-3587; Angew. Chem. Int. Ed. 2000, 39, 3442-3445;
8. c) H. Hisamoto, T. Saito, M. Tokeshi, A. Hibara, T. Kitamori, Chem. Commun. 2001, 2662-2663;
9. d) C. Wiles, P. Watts, S. J. Haswell, E. Pombo-Villar, Chem. Commun. 2002, 1034-1035;
10. e) T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, I. Ryu, Org. Lett. 2002, 4, 1691-1694;
11. f) E. Garcia-Egido, V. Spikmans, S. Y. F. Wong, B. H. Warrington, Lab Chip 2003, 3, 73-76;
12. g) M. Ueno, H. Hisamoto, T. Kitamori, S. Kobayashi, Chem. Commun. 2003, 936-937;
13. h) S. M. Lai, R. Martin-Aranda, K. L. Yeung, Chem. Commun. 2003, 218-219;
14. i) J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori, S. Kobayashi, Science 2004, 304, 1305-1308;
15. j) T. Wu, Y. Mei, J. T. Cabral, C. Xu, K. L. Beers, J. Am. Chem. Soc. 2004, 126, 9880-9881.
16. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
17. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
18. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
19. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
20. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
21. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
22. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
23. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
24. Example reviews: a) S. H. DeWitt, Curr. Opin. Chem. Biol. 1999, 3, 350-356; b) H. Okamoto, J. Syn. Org. Chem. Jpn. 1999, 57, 805-812; c) T. Sugawara, Pharmacia 2000, 36, 34-38; d) O. Wörz, K. P. Jäckel, T. Richter, A. Wolf, Chem. Eng. Sci. 2001, 56, 1029-1033; e) S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391-398; f) K. F. Jensen, Chem. Eng. Sci. 2001, 56, 293-303; g) A. de Mello, R. Wootton, Lab Chip 2002, 2, 7N-13N; h) K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410-451; Angew. Chem. Int. Ed. 2004, 43, 406-446.
25. S. Taghavi-Moghadam, A. Kleemann, K. G. Golbig, Org. Process Res. Dev. 2001, 5, 652-658.
26. a) R. D. Chambers, R. C. H. Spink, Chem. Commun. 1999, 883-884;
27. b) M. T. Janicke, H. Kestenbaum, U. Hagendorf, F. Schüth, M. Fichtner, K. Schubert, J. Catal. 2000, 191, 282-293;
28. c) M. W. Losey, M. A. Schmidt, K. F. Jensen, Ind. Eng. Chem. Res. 2001, 40, 2555-2562.
29. For example, a) S. Suga, M. Okajima, K. Fujiwara, J. Yoshida, J. Am. Chem. Soc. 2001, 123. 7941-7942; b) J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2651-2658; c) S. Suga, A. Nagaki, J. Yoshida, Chem. Commun. 2003, 354-355; d) S. Suga, A. Nagaki, Y. Tsutsui, J. Yoshida, Org. Lett. 2003, 5, 945-947; e) A. Nagaki, K. Kawamura, S. Suga, T. Ando, M. Sawamoto, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 14702-14703.
30. For example, a) S. Suga, M. Okajima, K. Fujiwara, J. Yoshida, J. Am. Chem. Soc. 2001, 123. 7941-7942; b) J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2651-2658; c) S. Suga, A. Nagaki, J. Yoshida, Chem. Commun. 2003, 354-355; d) S. Suga, A. Nagaki, Y. Tsutsui, J. Yoshida, Org. Lett. 2003, 5, 945-947; e) A. Nagaki, K. Kawamura, S. Suga, T. Ando, M. Sawamoto, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 14702-14703.
31. For example, a) S. Suga, M. Okajima, K. Fujiwara, J. Yoshida, J. Am. Chem. Soc. 2001, 123. 7941-7942; b) J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2651-2658; c) S. Suga, A. Nagaki, J. Yoshida, Chem. Commun. 2003, 354-355; d) S. Suga, A. Nagaki, Y. Tsutsui, J. Yoshida, Org. Lett. 2003, 5, 945-947; e) A. Nagaki, K. Kawamura, S. Suga, T. Ando, M. Sawamoto, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 14702-14703.
32. For example, a) S. Suga, M. Okajima, K. Fujiwara, J. Yoshida, J. Am. Chem. Soc. 2001, 123. 7941-7942; b) J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2651-2658; c) S. Suga, A. Nagaki, J. Yoshida, Chem. Commun. 2003, 354-355; d) S. Suga, A. Nagaki, Y. Tsutsui, J. Yoshida, Org. Lett. 2003, 5, 945-947; e) A. Nagaki, K. Kawamura, S. Suga, T. Ando, M. Sawamoto, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 14702-14703.
33. For example, a) S. Suga, M. Okajima, K. Fujiwara, J. Yoshida, J. Am. Chem. Soc. 2001, 123. 7941-7942; b) J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2651-2658; c) S. Suga, A. Nagaki, J. Yoshida, Chem. Commun. 2003, 354-355; d) S. Suga, A. Nagaki, Y. Tsutsui, J. Yoshida, Org. Lett. 2003, 5, 945-947; e) A. Nagaki, K. Kawamura, S. Suga, T. Ando, M. Sawamoto, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 14702-14703.
34. For example, T. T. Tidwell, Org. React. 1990, 39, 297-572.
35. a) K. Omura, A. K. Sharma, D. Swern, J. Org. Chem. 1976, 41, 957-962;
36. b) K. Omura, D. Swern, Tetrahedron 1978, 34, 1651-1660.
37. a) A. K. Sharma, D. Swern, Tetrahedron Lett. 1974, 1503-1506;
38. b) A. K. Sharma, T. Ku, A. D. Dawson, D. Swern, J. Org. Chem. 1975, 40, 2758-2764.
39. The IMM (Institut für Mikrotechnik Mainz GmbH) single mixer. version 2, (http://www.imm-mainz.de/) was used. The inlay is made of silver and the channel width is 40 μm.
40. The Harvard PHD2000 Programmable syringe pump. Harvard Pump11 (http://www.harvardapparatus.com/), and kdScientific model 100 syringe pump (http://www.kdscientific.com/) were used.