A practical and mild method for the highly selective conversion of terminal alkenes into aldehydes through epoxidation-isomerization with ruthenium(IV)-porphyrin catalysts

Angewandte Chemie - International Edition

Volumn 43, Issue 37, 2004, Pages 4950-4954

  Chen, Jian ^a   Che, Chi Ming ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Homogeneous catalysis; Metalloporphyrins; N ligands; Oxidation; Ruthenium

Indexed keywords

ALDEHYDES; CATALYSIS; ETHANOL; OXIDATION; RUTHENIUM; STRUCTURE (COMPOSITION);

OLEFINATION; SELECTIVE CONVERSION;

OLEFINS;

2,6 DICHLOROPYRIDINE N OXIDE; ALDEHYDE; ALKENE; CHLORINE DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; PORPHYRIN DERIVATIVE; PYRIDINE 1 OXIDE; RUTHENIUM COMPLEX; RUTHENIUM PORPHYRIN COMPLEX; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; EPOXIDATION; ISOMERIZATION; OLEFINATION; SYNTHESIS;

EID: 4744345859     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460545     Document Type: Article

References (48)

1. a) J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, R. Rüttinger, H. Kojer, Angew. Chem. 1959, 71, 176-182;
2. b) J. Smidt, W. Hafner, R. Jira, R. Sieber, J. Sedlmeier, A. Sabel, Angew. Chem. 1962, 74, 93-102; Angew. Chem. Int. Ed. Engl. 1962, 1, 80-88;
3. b) J. Smidt, W. Hafner, R. Jira, R. Sieber, J. Sedlmeier, A. Sabel, Angew. Chem. 1962, 74, 93-102; Angew. Chem. Int. Ed. Engl. 1962, 1, 80-88;
4. c) J. Tsuji, Synthesis 1984, 369-384;
5. (d) J. Tsuji, Palladium Reagents and Catalysts: Innovation in Organic Synthesis, Wiley, New York, 1998.
6. a) B. L. Feringa, J. Chem. Soc. Chem. Commun. 1986, 909-910;
7. b) T. Hosokawa, S. Aoki, M. Takano, T. Nakahira, Y. Yoshida, S.-I. Murahashi, J. Chem. Soc. Chem. Commun. 1991, 1559-1560;
8. c) T. T. Wenzel, J. Chem. Soc. Chem. Commun. 1993, 862-864;
9. (d) T.-L. Ho, M. H. Chang, C. Chen, Tetrahedron Lett. 2003, 44, 6955-6957.
10. 2tmp = meso-tetramesitylporphyrin.
11. 2pyNO or air catalyzed by ruthenium porphyrins, only small or trace amounts of aldehydes, if any, were formed; see, for example: a) H. Ohtake, T. Higuchi, M. Hirobe, Heterocycles 1995, 40, 867-903;
12. b) J. T. Groves, M. Bonchio, T. Carofiglio, K. Shalyaev, J. Am. Chem. Soc. 1996,118, 8961-8962;
13. c) A. Berkessel, M. Frauenkron, J. Chem. Soc. Perkin Trans. 1 1997, 2265-2266;
14. (d) T.-S. Lai, R. Zhang, K.-K. Cheung, H.-L. Kwong, C.-M. Che, Chem. Commun. 1998, 1583-1584;
15. e) C.-J. Liu, W.-Y. Yu, S.-G. Li, C.-M. Che, J. Org. Chem. 1998, 63, 7364-7369;
16. f) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080;
17. g) Z. Gross, S. Ini, Inorg. Chem. 1999, 38, 1446-1449;
18. h) X.-Q. Yu, J.-S. Huang, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2000, 122, 5337-5342;
19. i) R. Zhang, W.-Y. Yu, K.-Y. Wong, C.-M. Che, J. Org. Chem. 2001, 66, 8145-8153;
20. j) J.-L. Zhang, H.-B. Zhou, J.-S. Huang, C.-M. Che, Chem. Eur. J. 2002, 8, 1554-1562;
21. k) J.-L. Zhang, C.-M. Che, Org. Lett. 2002, 4, 1911-1914;
22. l) J.-L. Zhang, Y.-L. Liu, C.-M. Che, Chem. Commun. 2002, 2906-2907;
23. m) A. Berkessel, P. Kaiser, J. Lex, Chem. Eur. J. 2003, 9, 4746-4756;
24. (n) P. Le Maux, M. Lukas, G. Simonneaux, J. Mol. Catal. A 2003, 206, 95-103.
25. 8tpfpp = octachlorotetrakis(penta-fluorophenyl)porphyrin) primarily affords benzaldehyde, a C= C bond-cleavage product; see: E. R. Birnbaum, J. A. Labinger, J. E. Bercaw, H. B. Gray, Inorg. Chim. Acta 1998, 270, 433-439.
26. 2tpp = meso-tetraphenylporphyrin) were previously reported to be good reagents or catalysts for the isomerization of epoxides to form aldehydes; see, for example: a) H. Alper, D. Des Roches, T. Durst, R. Legault, J. Org. Chem. 1976, 41, 3611-3613;
27. b) R. Sudha, K. M. Narasimhan, V. G. Saraswathy, S. Sankararaman, J. Org. Chem. 1996, 61, 1877-1879;
28. c) S. Kulasegaram, R. J. Kulawiec, J. Org. Chem. 1997, 62, 6547-6561;
29. (d) B. C. Ranu, U. Jana, J. Org. Chem. 1998, 63, 8212-8216;
30. e) K. Suda, K. Baba, S. Nakajima, T. Takanami, Tetrahedron Lett. 1999, 40, 7243-7246;
31. f) F. Martínez, C. del Campo, E. F. Llama, J. Chem. Soc. Perkin Trans. 1 2000, 1749-1751.
32. II(tmp)(CO)] during the epoxidation of alkenes: B. Scharbert, E. Zeisberger, E. Paulus, J. Organomet. Chem. 1995, 493, 143-147.
33. The oxidation of styrene with iodosylbenzenes or tert-butyl hydroperoxide catalyzed by metal complexes, including iron/manganese porphyrins or corroles, also affords a mixture of styrene oxide and 27, with the former being the major product; see, for example: a) J. P. Collman, T. Kodadek, J. I. Brauman, J. Am. Chem. Soc. 1986, 108, 2588-2594;
34. b) J. F. Kinneary, J. S. Albert, C. J. Burrows, J. Am. Chem. Soc. 1988, 110, 6124-6129;
35. c) F. Minisci, F. Fontana, S. Araneo, F. Recupero, S. Banfi, S. Quici, J. Am. Chem. Soc. 1995, 117, 226-232;
36. (d) Z. Gross, G. Golubkov, L. Simkhovich, Angew. Chem. 2000, 112, 4211-4213; Angew. Chem. Int. Ed. 2000, 39, 4045-4047;
37. (d) Z. Gross, G. Golubkov, L. Simkhovich, Angew. Chem. 2000, 112, 4211-4213; Angew. Chem. Int. Ed. 2000, 39, 4045-4047;
38. e) G. Golubkov, J. Bendix, H. B. Gray, A. Mahammed, I. Goldberg, A. J. Dibilio, Z. Gross, Angew. Chem. 2001, 113, 2190-2192; Angew. Chem. Int. Ed. 2001, 40, 2132-2134.
39. e) G. Golubkov, J. Bendix, H. B. Gray, A. Mahammed, I. Goldberg, A. J. Dibilio, Z. Gross, Angew. Chem. 2001, 113, 2190-2192; Angew. Chem. Int. Ed. 2001, 40, 2132-2134.
40. a) G. A. Mirafzal, G. Cheng, L. K. Woo, J. Am. Chem. Soc. 2002, 124, 176-177;
41. b) V. K. Aggarwal, J. R. Fulton, C. G. Sheldon, J. de Vicente, J. Am. Chem. Soc. 2003, 125, 6034-6035;
42. c) Y. Chen, L. Huang, M. A. Ranade, X. P. Zhang, J. Org. Chem. 2003, 68, 3714-3717.
43. For selected examples, see: a) C. G. Kruse, J. P. Bouw, R. van Hes, A. van de Kuilen, J. A. J. den Hartog, Heterocycles 1987, 26, 3141-3151;
44. b) G. A. Molander, S. W. Andrews, Tetrahedron Lett. 1989, 30, 2351-2354;
45. c) G. A. Molander, K. O. Cameron, J. Org. Chem. 1991, 56, 2617-2619;
46. (d) G. A. Molander, K. O. Cameron, J. Am. Chem. Soc. 1993, 115, 830-846;
47. e) F. Manescalchi, A. R. Nardi, D. Savoia, Tetrahedron Lett. 1994, 35, 2775-2778;
48. f) K. Okada, K. Matsumoto, K. Oshima, K. Utimoto, Tetrahedron Lett. 1995, 36, 8067-8070.