Dual functionalities of hydrogen-bonding self-assembled catalysts in chelation-assisted hydroacylation

Journal of Organic Chemistry

Volumn 73, Issue 14, 2008, Pages 5598-5601

  Park, Jung Woo ^a   Park, Ji Hye ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ASSEMBLY; CATALYSTS; CHELATION; COMPLEXATION; HYDROGEN; HYDROGEN BONDS; NONMETALS; OLEFINS; PHOSPHORUS COMPOUNDS; RHODIUM; RHODIUM COMPOUNDS;

AMERICAN CHEMICAL SOCIETY (ACS); DIAMINOPYRIDINE (DAP); HOMOGENEOUS CATALYSTS; HYDROACYLATION; HYDROGEN BONDINGS; PRIMARY ALCOHOLS; RHODIUM(I); SELF-ASSEMBLED; SUPRAMOLECULAR ASSEMBLIES;

CATALYSIS;

ALCOHOL; ALKENE; BARBITURIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; RHODIUM COMPLEX;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHELATION; CHEMICAL REACTION; COOLING; HEATING; HYDROGEN BOND; SUPRAMOLECULAR CHEMISTRY;

ACYLATION; CATALYSIS; CHELATING AGENTS; HYDROGEN; HYDROGEN BONDING; MOLECULAR STRUCTURE;

EID: 48249084529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800862q     Document Type: Article

References (49)

1. (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
2. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
3. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
4. (d) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S. Ed.; Springer: Berlin, 1999; p 97.
5. (e) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
6. (f) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
7. (g) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
8. (h) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
9. (i) Godula, K.; Sames, D. Science 2006, 312, 67.
10. (a) Willis, M. C.; McNally, S. J.; Beswick, P. J. Angew. Chem., Int. Ed. 2004, 43, 340.
11. (b) Willis, M. C.; Randell-Sly, H. E.; Woodward, R. L.; Currie, G. S. Org. Lett. 2005, 7, 2249.
12. (c) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564.
13. (d) Tanaka, M.; Imai, M.; Yamamoto, Y.; Tanaka, K.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H. Org. Lett. 2003, 5, 1365.
14. (e) Imai, M.; Tanaka, M.; Tanaka, K.; Yamamoto, Y.; Imai-Ogata, N.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H. J. Org. Chem. 2004, 69, 1144.
15. (f) Tanaka, K.; Tanaka, M.; Suemune, H. Tetrahedron Lett. 2005, 46, 6053.
16. Our recent account on chelation-assisted C-H and C-C bond activation and its application to recyclable catalysis: Park, Y. J.; Park. J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222.
17. (a) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200.
18. (b) Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hong, J.-B. Angew. Chem., Int. Ed. 2000, 39, 3070.
19. (c) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. - Eur. J. 2002, 8, 2423.
20. (d) Jun, C.-H.; Jo, E.-A.; Park. J.-W. Eur. J. Org. Chem. 2007, 1869.
21. (a) Jun, C.-H.; Huh, C.-W.; Na, S.-J. Angew. Chem., Int. Ed. 1998, 37, 145.
22. (b) Jun, C.-H.; Hwang, D.-C. Polymer 1998, 39, 7143.
23. Special issue on recoverable catalysts and reagents: Chem. Rev. 2002, 102, 3215-3892.
24. (a) Bergbreiter, D. E. Catal. Today 1998, 42, 389.
25. (b) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531.
26. (c) Wentworth, P., Jr.; Janda, K. D. Chem. Commun. 1999, 1917.
27. (d) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101.
28. (e) Schlenk, C.; Kleij, A. W.; Frey, H.; van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 3445.
29. (f) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058.
30. (g) Bergbreiter, D. E.; Osburn, P. L.; Frels, J. D. J. Am. Chem. Soc. 2001, 123, 11105.
31. Recent review on dendrimers in catalysis: Oosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. 2001, 40, 1829.
32. Lindner, E.; Schneller, T.; Auer, F.; Mayer, H. A. Angew. Chem., Int. Ed. 1999, 38, 2154.
33. (a) Yoshida, J.-i.; Itami, K. Chem. Rev. 2002, 102, 3693.
34. (b) de Groot, D.; de Waal, B. F. M.; Reek, J. N. H.; Schenning, A. P. H. J.; Kamer, P. C. J.; Meijer, E. W.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2001, 123, 8453.
35. (c) Chen, R.; Bronger, R. P. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. J. Am. Chem. Soc. 2004, 126, 14557.
36. (d) Yang, J.; Ding, S.; Radosz, M.; Shen, Y. Macromolecules 2004, 37, 1728.
37. (e) Davies, H. M. L.; Walji, A. M.; Nagashima, T. J. Am. Chem. Soc. 2004, 126, 4271.
38. Jun, C.-H.; Hong, H.-S.; Huh. C.-W. Tetrahedron Lett. 1999, 40, 8897.
39. Chang, D.-H.; Lee, D.-Y.; Hong, B.-S.; Choi, J.-H.; Jun, C.-H. J. Am. Chem. Soc. 2004, 126, 424.
40. (a) Kim, D.-W.; Lim, S.-G.; Jun, C.-H. Org. Lett. 2006, 8, 2937.
41. For orthoalkylation: (b) Yoon, J. H.; Park, Y. J.; Lee, J. H.; Yoo, J.; Jun, C.-H. Org. Lett. 2005, 7, 2889.
42. 2 (1a, 40 mol %), TP (2a, 40 mol %), cyclohexylamine (10 mol %), and benzoic acid (20 mol %) in 1,4-dioxane at 130°C to afford 6a in a 24% GC yield after 1 h.
43. Several reports of hydrogen-bonding network of 2b derivatives with barbiturates: (a) Chang, S. K.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 1318.
44. (b) Chang, S. K.; Engen, D. V.; Fan, E.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 7640.
45. (c) Motesharei, K.; Myles, D. C. J. Am. Chem. Soc. 1998, 120, 7328.
46. (d) Al-Sayah, M. H.; McDonald, R.; Branda, N. R. Eur. J. Org. Chem. 2004, 173.
47. Knizek, J.; Krossing, I.; Nöth, H.; Plener, V.; Schmidt, M.; Weigand, W. Z. Naturforsch. B 1998, 53b, 1135.
48. Yamada, Y. M. A.; Maeda, Y.; Uozumi, Y. Org. Lett. 2006, 8, 4259.
49. 2 and benzoic acid are additives for accelerating the hydroacylation reaction.