Catalysis and regioselectivity of the aqueous Heck reaction by Pd(0) nanoparticles under ultrasonic irradiation

Journal of Organic Chemistry

Volumn 71, Issue 11, 2006, Pages 4339-4342

  Zhang, Zuhui ^a   Zha, Zhenggen ^a   Gan, Changsheng ^a   Pan, Chongfeng ^a   Zhou, Yuqing ^a   Wang, Zhiyong ^a   Zhou, Ming Ming ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS HECK REACTION; ELECTRON-DONATING; PHENYL IODIDES; REGIOSELECTIVITY; ULTRASONIC IRRADIATION;

CATALYSIS; IRRADIATION; NANOSTRUCTURED MATERIALS; SUBSTITUTION REACTIONS; TRANSMISSION ELECTRON MICROSCOPY; ULTRASONIC WAVES; X RAY POWDER DIFFRACTION;

PALLADIUM;

ACRYLIC ACID METHYL ESTER; CARBON; IODIDE; IODINE; IODOBENZENE; NANOPARTICLE; PALLADIUM;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL ENVIRONMENT; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; HECK REACTION; REACTION ANALYSIS; REGIOSELECTIVITY; TRANSMISSION ELECTRON MICROSCOPY; ULTRASOUND; X RAY DIFFRACTION;

CATALYSIS; NANOPARTICLES; PALLADIUM; ULTRASONICS; WATER;

EID: 33646949476     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060372b     Document Type: Article

References (65)

1. (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
2. (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
3. For selected reviews of Heck reaction, see: (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
4. (b) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
5. (c) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
6. (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
7. (e) Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1.
8. (f) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
9. (g) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
10. (h) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
11. (i) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1995, 33, 2379.
12. (j) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
13. For a general introduction to organic reactions in water, see: (a) Li, C. J. Chem. Rev. 2005, 105, 3095.
14. (b) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
15. (c) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
16. (d) Li, C. J. Chem. Rev. 1993, 93, 2023.
17. (e) Genet, J.-P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305.
18. For recent examples, see: (a) Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2005, 70, 1786.
19. (b) Hagiwara, H.; Sugawara, Y.; Hoshi, T.; Suzuki, T. Chem. Commun. 2005, 2942.
20. (c) Bhattacharya, S.; Srivastavaa, A.; Sengupta, S. Tetrahedron Lett. 2005, 46, 3557.
21. (d) Botella, L.; Nájera, C. Tetrahedron Lett. 2004, 45, 1833.
22. (e) Solabannavar, S. B.; Desai, U. V.; Mane, R. B. Green Chem. 2002, 4, 347.
23. (f) Mukhopadhyay, S.; Rothenberg, G.; Joshi, A.; Baidossi, M.; Sasson, Y. Adv. Synth. Catal. 2002, 344, 348.
24. (g) Ansos, M. S.; Mirza, A. R.; Tonks, L.; William, J. M. J. Tetrahedron Lett. 1999, 40, 7147.
25. (h) Uozumi, Y.; Kimura, T. Synlett 2002, 2045.
26. (i) Botella, L.; Nájera, C. J. Org. Chem. 2005, 70, 4360.
27. (j) Nájera, C.; Gil-moltó, J.; Karlström, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451.
28. (k) Jeffery, T. Tetrahedron 1996, 52, 10113.
29. Heck couplings proceeding in organic solvent at room temperature in the presence of air-sensitive phosphine ligands or catalyzed by chloropalladated propargylamine were reported, see: (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
30. (b) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677.
31. (c) Consorti, C. S.; Zanini, M. L.; Leal, S.; Ebeling, G.; Dupont, J. Org. Lett. 2003, 5, 983.
32. Regioselective couplings at the α-position of an olefin double bond were reported, see: (a) Mo, J.; Xu, L. J.; Xiao, J. L. J. Am. Chem. Soc. 2005, 127, 751.
33. (b) Svennebring, A.; Nilsson, P.; Larhed, M. J. Org. Chem. 2004, 69, 3345.
34. (c) Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2003, 125, 3430.
35. (d) Glorius, F. Tetrahedron Lett. 2003, 44, 5751.
36. (e) Barcia, J. C.; Cruces, J.; Estévez, J. C.; Estévez, R. J.; Castedo, L. Tetrahedron Lett. 2002, 43, 5141.
37. (f) Ishiyama, T.; Hartwig, J. J. Am. Chem. Soc. 2000, 122, 12043.
38. (g) Huang, Y. C.; Majumdar, K. K.; Cheng, C. H. J. Org. Chem. 2002, 67, 1682.
39. (h) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488.
40. Ultrasound-promoted Heck reaction and Sonogashi reaction in room-temperature ionic liquids were reported, see: (a) Deshmukh, R. R.; Rajagopal, R.; Srinivasan, K. V. Chem. Commun. 2001, 1544.
41. (b) Gholap, A. R.; Venkatesan, K.; Pasricha, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2005, 70, 4869.
42. For a Heck coupling assisted by ultrasound in NMP using Pd/C, see: Ambulgekar, G. V.; Bhanage, B. M.; Samant, S. D. Tetrahedron Lett. 2005, 46, 2483.
43. Several reviews about nano catalysis were reported, see: (a) Roucoux, A.; Schulz, J.; Patin, H. Chem. Rev. 2002, 102, 3757.
44. (b) Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852.
45. (c) Moreno-Mañas, M.; Pleixats, R. Acc. Chem. Res. 2003, 36, 638.
46. For recent reports on nano-Pd catalyst organic reactions, see: (a) Chung M.-K.; Schlaf, M. J. Am. Chem. Soc. 2004, 126, 7386.
47. (b) Jansat, S.; Gómez, M.; Philippot, K.; Muller, G.; Guiu, E.; Claver, C.; Castillón, S.; Chaudret, B. J. Am. Chem. Soc. 2004, 126, 1592.
48. (c) Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Nano Lett. 2002, 2, 999.
49. (d) Calò, V.; Nacci, A.; Monopoli, A.; Montingelli, F. J. Org. Chem. 2005, 70, 6040.
50. (e) Schmidt, B. Chem. Commun. 2003, 1654.
51. (f) Luo, C. C.; Hiroyuki, O.; Wai, C. M.; Kim, H.; Kim, J.; Ohde, M. J. Am. Chem. Soc. 2002, 124, 4550.
52. For recent reports on nano-Pd catalyst Heck reaction, see: (a) Cassol, C. C.; Umpierre, A. P.; Machado, G.; Wolke, S. I.; Dupont, J. J. Am. Chem. Soc. 2005, 127, 3298.
53. (b) Zhang, Y. H.; Wang, Y. G. J. Mol. Catal. A: Chem. 2005, 229, 7.
54. (c) Caló, V.; Nacci, A.; Monopoli, A.; Laera, S.; Cioffi, N. J. Org. Chem. 2003, 68, 2929.
55. (d) Kim, S.-W.; Kim, M.; Lee, W. Y.; Hyeon, T. J. Am. Chem. Soc. 2002, 124, 7642.
56. (e) Yeung, L. K.; Crooks, R. M. Nano Lett. 2001, 1, 14.
57. (a) Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165.
58. (b) Reetz, M. T.; Maase, M. Adv. Mater. 1999, 11, 773.
59. (a) Fujimoto, T.; Terauchi, S.-Y.; Umehara, H.; Kojima, I.; Henderson, W. Chem. Mater. 2001, 13, 1057.
60. (b) Okitsu, K.; Yue, A.; Tanabe, S.; Matsumoto, H. Chem. Mater. 2000, 12, 3006.
61. The XRD patterns have three characteristic dihedrals: 40.119, 46.659, and 68.125, with the relative intensities of 100%, 60%, and 42%, respectively.
62. (a) Mason, T. J.; Peters, D. Practical Sonochemistry, 2nd ed.; Ellis Horwood, London, 2002.
63. (b) Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press: New York, 1998.
64. The role of PTC in Heck reaction has been systematically studied by Jeffery, see: Jeffery, T. Tetrahedron 1996, 52, 10113.
65. The catalysts can be recovered by extracting the mixture with petroleum ether (see Supporting Information).