A multipolymer system for organocatalytic alcohol oxidation

Organic and Biomolecular Chemistry

Volumn 3, Issue 6, 2005, Pages 970-971

  But, Tracy Yuen Sze ^a   Tashino, Yousuke ^b   Togo, Hideo ^b   Toy, Patrick H ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AROMATIC POLYMERS; KETONES; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; OXIDATION; PURIFICATION; REACTION KINETICS; RECYCLING; SILICA; SUBSTRATES;

2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY (TEMPO); AROMATIC ALCOHOLS; MULTIPOLYMER SYSTEM; ORGANOCATALYTIC ALCOHOL; POLYMERIC REAGENTS; POLYSTYRENE-SUPPORTED DIACETOXYIODOSOBENZENE (1, PSDIB);

CATALYSIS;

EID: 16244371720     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500965k     Document Type: Article

References (49)

1. (a) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815;
2. (b) S. Bräse, F. Lauterwasser and R. E. Ziegert, Adv. Synth. Catal., 2003, 345, 869.
3. M. Benaglia, A. Puglisi and F. Cozzi, Chem. Rev., 2003, 103, 3401.
4. (a) G. Cainelli, M. Contento, F. Manescalchi and R. Regnoli, J. Chem. Soc., Perkin Trans. 1, 1980, 2516;
5. (b) B. J. Cohen, M. A. Kraus and A. Patchornik, J. Am. Chem. Soc., 1981, 103, 7620;
6. (c) D. E. Bergbreiter and R. Chandran, J. Am. Chem. Soc., 1985, 107, 4792;
7. (d) M. Bessodes and K. Antonakis, Tetrahedron Lett., 1985, 26, 1305;
8. (e) S. L. Regen and M. Kodomari, J. Chem. Soc., Chem. Commun., 1987, 1428;
9. (f) J. J. Parlow, Tetrahedron Lett., 1995, 36, 1395.
10. (a) For examples of substrates being detached from one polymer in order to react with a different polymeric reagent, see; A. Warshawsky, R. Kalir and A. Patchornik, J. Am. Chem. Soc., 1978, 100, 4544; (b) J. Rebek, Jr., Tetrahedron, 1979, 35, 723; (c) Y. Hamuro, M. A. Scialdone and W. F. DeGrado, J. Am. Chem. Soc., 1999, 121, 1636; (d) M. Gravel, K. A. Thompson, M. Zak, C. Beruhe and D. G. Hall, J. Org. Chem., 2002, 67, 3; (e) J. C. Pelletier, A. Khan and Z. Tang, Org. Lett., 2002, 4, 4611.
11. (a) For examples of substrates being detached from one polymer in order to react with a different polymeric reagent, see; A. Warshawsky, R. Kalir and A. Patchornik, J. Am. Chem. Soc., 1978, 100, 4544; (b) J. Rebek, Jr., Tetrahedron, 1979, 35, 723; (c) Y. Hamuro, M. A. Scialdone and W. F. DeGrado, J. Am. Chem. Soc., 1999, 121, 1636; (d) M. Gravel, K. A. Thompson, M. Zak, C. Beruhe and D. G. Hall, J. Org. Chem., 2002, 67, 3; (e) J. C. Pelletier, A. Khan and Z. Tang, Org. Lett., 2002, 4, 4611.
12. (a) For examples of substrates being detached from one polymer in order to react with a different polymeric reagent, see; A. Warshawsky, R. Kalir and A. Patchornik, J. Am. Chem. Soc., 1978, 100, 4544; (b) J. Rebek, Jr., Tetrahedron, 1979, 35, 723; (c) Y. Hamuro, M. A. Scialdone and W. F. DeGrado, J. Am. Chem. Soc., 1999, 121, 1636; (d) M. Gravel, K. A. Thompson, M. Zak, C. Beruhe and D. G. Hall, J. Org. Chem., 2002, 67, 3; (e) J. C. Pelletier, A. Khan and Z. Tang, Org. Lett., 2002, 4, 4611.
13. (a) For examples of substrates being detached from one polymer in order to react with a different polymeric reagent, see; A. Warshawsky, R. Kalir and A. Patchornik, J. Am. Chem. Soc., 1978, 100, 4544; (b) J. Rebek, Jr., Tetrahedron, 1979, 35, 723; (c) Y. Hamuro, M. A. Scialdone and W. F. DeGrado, J. Am. Chem. Soc., 1999, 121, 1636; (d) M. Gravel, K. A. Thompson, M. Zak, C. Beruhe and D. G. Hall, J. Org. Chem., 2002, 67, 3; (e) J. C. Pelletier, A. Khan and Z. Tang, Org. Lett., 2002, 4, 4611.
14. (a) For examples of substrates being detached from one polymer in order to react with a different polymeric reagent, see; A. Warshawsky, R. Kalir and A. Patchornik, J. Am. Chem. Soc., 1978, 100, 4544; (b) J. Rebek, Jr., Tetrahedron, 1979, 35, 723; (c) Y. Hamuro, M. A. Scialdone and W. F. DeGrado, J. Am. Chem. Soc., 1999, 121, 1636; (d) M. Gravel, K. A. Thompson, M. Zak, C. Beruhe and D. G. Hall, J. Org. Chem., 2002, 67, 3; (e) J. C. Pelletier, A. Khan and Z. Tang, Org. Lett., 2002, 4, 4611.
15. (a) P. H. Toy and K. D. Janda, Acc. Chem. Res., 2000, 33, 546;
16. (b) T. J. Dickerson, N. N. Reed and K. D. Janda, Chem. Rev., 2002, 102, 3325;
17. (c) D. E. Bergbreiter, Chem. Rev., 2002, 102, 3345.
18. (a) For examples of soluble polymer-supported reagents or substrates reacting with insoluble polymer-supported reagents or substrates, see: H. Frank and H. Hagenmaier, Experientia, 1975, 31, 131; (b) G. Heusei, G. Bovermann, W. Göhring and G. Kung, Angew. Chem., Int. Ed. Engl., 1977, 16, 642; (c) D. E. Bergbreiter and R. Chandran, J. Am. Chem. Soc., 1987, 109, 174; (d) H. Han and K. D. Janda, Angew. Chem. Int. Ed. Engl., 1997, 36, 1731; (e) P. H. Toy, T. S. Reger and K. D. Janda, Org. Lett:, 2000, 2, 2205.
19. (a) For examples of soluble polymer-supported reagents or substrates reacting with insoluble polymer-supported reagents or substrates, see: H. Frank and H. Hagenmaier, Experientia, 1975, 31, 131; (b) G. Heusei, G. Bovermann, W. Göhring and G. Kung, Angew. Chem., Int. Ed. Engl., 1977, 16, 642; (c) D. E. Bergbreiter and R. Chandran, J. Am. Chem. Soc., 1987, 109, 174; (d) H. Han and K. D. Janda, Angew. Chem. Int. Ed. Engl., 1997, 36, 1731; (e) P. H. Toy, T. S. Reger and K. D. Janda, Org. Lett:, 2000, 2, 2205.
20. (a) For examples of soluble polymer-supported reagents or substrates reacting with insoluble polymer-supported reagents or substrates, see: H. Frank and H. Hagenmaier, Experientia, 1975, 31, 131; (b) G. Heusei, G. Bovermann, W. Göhring and G. Kung, Angew. Chem., Int. Ed. Engl., 1977, 16, 642; (c) D. E. Bergbreiter and R. Chandran, J. Am. Chem. Soc., 1987, 109, 174; (d) H. Han and K. D. Janda, Angew. Chem. Int. Ed. Engl., 1997, 36, 1731; (e) P. H. Toy, T. S. Reger and K. D. Janda, Org. Lett:, 2000, 2, 2205.
21. (a) For examples of soluble polymer-supported reagents or substrates reacting with insoluble polymer-supported reagents or substrates, see: H. Frank and H. Hagenmaier, Experientia, 1975, 31, 131; (b) G. Heusei, G. Bovermann, W. Göhring and G. Kung, Angew. Chem., Int. Ed. Engl., 1977, 16, 642; (c) D. E. Bergbreiter and R. Chandran, J. Am. Chem. Soc., 1987, 109, 174; (d) H. Han and K. D. Janda, Angew. Chem. Int. Ed. Engl., 1997, 36, 1731; (e) P. H. Toy, T. S. Reger and K. D. Janda, Org. Lett:, 2000, 2, 2205.
22. (a) For examples of soluble polymer-supported reagents or substrates reacting with insoluble polymer-supported reagents or substrates, see: H. Frank and H. Hagenmaier, Experientia, 1975, 31, 131; (b) G. Heusei, G. Bovermann, W. Göhring and G. Kung, Angew. Chem., Int. Ed. Engl., 1977, 16, 642; (c) D. E. Bergbreiter and R. Chandran, J. Am. Chem. Soc., 1987, 109, 174; (d) H. Han and K. D. Janda, Angew. Chem. Int. Ed. Engl., 1997, 36, 1731; (e) P. H. Toy, T. S. Reger and K. D. Janda, Org. Lett:, 2000, 2, 2205.
23. For a report of two different soluble-polymer bound substrates reacting with one another in a convergent and combinatorial manner, see: J.-M. Ahn, R Wentworth, Jr. and K. D. Janda, Chem. Commun., 2003, 480.
24. X. H. Ouyang, R. W. Armstrong and M. M. Murphy, J. Org. Chem., 1998, 63, 1027.
25. K. Yasuda and S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 2002, 1024.
26. A. M. Harned, H. S. He, P. H. Toy, D. L. Flynn and P. R. Hanson, J. Am. Chem. Soc., 2005, 127, 52.
27. J. T. W Kan and P. H. Toy, Tetrahedron Lett., 2004, 45, 6357.
28. (a) M. K. W. Choi and P. H. Toy, Tetrahedron, 2003, 59, 7171;
29. (b) M. K. W. Choi and P. H. Toy, Tetrahedron, 2004, 60, 2875.
30. For a review of polymer-supported hypervalent iodine reagents, see: H. Togo and K. Sakuratani, Synlett, 2002, 1966. For a review of hypervalent iodine reagents in oxidation reactions, see:; H. Tohma and Y. Kita, Adv. Synth. Catal., 2004, 346, 111.
31. For a review of polymer-supported hypervalent iodine reagents, see: H. Togo and K. Sakuratani, Synlett, 2002, 1966. For a review of hypervalent iodine reagents in oxidation reactions, see:; H. Tohma and Y. Kita, Adv. Synth. Catal., 2004, 346, 111.
32. (a) S. V. Ley, A. W. Thomas and H. Finch, J. Chem. Soc., Perkin Trans. 1, 1999, 669;
33. (b) H. Tohma, S. Takizawa, T. Maegawa and Y. Kita, Angew. Chem., Int. Ed., 2000, 39, 1306;
34. (c) S. Ficht, M. Mülbaier and A. Giannis, Tetrahedron, 2001, 57, 4863.
35. (a) H. Togo, G. Nogami and M. Yokoyama, Synlett, 1998, 534;
36. (b) H. Togo, S. Abe, G. Nogami and M. Yokoyama, Bull Chem. Soc. Jpn., 1999, 72, 2351;
37. (c) K. Sakuratani and H. Togo, ARKIVOC, 2003, 11.
38. J.-M. Chen and X. Huang, Synthesis, 2004, 2459.
39. For a review of nitroxyl radical mediated oxidation reactions, see: R. A. Sheldon and I. W. C. E. Arends, Adv. Synth. Catal., 2004, 346, 1051.
40. K. Sakuratani and H. Togo, Synthesis, 2003, 21.
41. Y. Tashino and H. Togo, Synlett, 2004, 2010.
42. A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Synlett, 2001, 102.
43. (a) C. Tanyeli and A. Gumus, Tetrahedron Lett., 2003, 44, 1639;
44. (b) G. Pozzi, M. Cavazzini, S. Quici, M. Benaglia and G. Dell'Anna, Org. Lett., 2004, 6, 441;
45. (c) P. Ferreira, W. Hayes, E. Phillips, D. Rippon and S. C. Tsang, Green Chem., 2004, 6, 310;
46. (d) P. Ferreira, E. Phillips, D. Rippon, S. C. Tsang and W. Hayes, J. Org. Chem., 2004, 69, 6851.
47. (a) P. H. Toy and K. D. Janda, Tetrahedron Lett., 1999, 40, 6329;
48. (b) P. H. Toy, T. S. Reger, P. Garibay, J. C. Garno, J. A. Malikayil, G.-Y. Liu and K. D. Janda, J. Comb. Chem., 2001, 3, 117;
49. (c) L.-J. Zhao, H. S. He, M. Shi and P. H. Toy, J. Comb. Chem., 2004, 6, 680.