Anchored palladium bipyridyl complex in nanosized MCM-41: a recyclable and efficient catalyst for the Kumada-Corriu reaction

Tetrahedron

Volumn 63, Issue 20, 2007, Pages 4304-4309

  Tsai, Fu Yu ^a   Lin, Bo Nan ^a   Chen, Ming Jie ^a   Mou, Chung Yuan ^b   Liu, Shiuh Tzung ^b  

^a NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Kumada Corriu reaction; Mesoporous silica; Palladium bipyridyl complex; Recyclable catalyst

Indexed keywords

2 (2 METHOXYPHENYL)THIOPHENE; 2 (4 CHLOROPHENYL)THIOPHENE; 2 METHOXYBIPHENYL; 2 PHENYLTHIOPHENE; 2,2' BITHIENYL; 2,3' BITHIENYL; 2,4 TOLYLTHIOPHENE; 3 (4 METHOXYPHENYL)THIOPHENE; 3 PHENYLTHIOPHENE; 4 CHLOROBIPHENYL; 4 METHOXYBIPHENYL; 4 METHYLBIPHENYL; 4' CHLORO 4 METHOXYBIPHENYL; 4' METHOXY 2,4,6 TRIMETHYLBIPHENYL; 4' METHOXY 4 METHYLBIPHENYL; 4,4' DIMETHOXYBIPHENYL; BIPHENYL; BIPHENYL DERIVATIVE; BIPYRIDINE DERIVATIVE; BROMINE DERIVATIVE; DIPHENYLMETHANE; IODINE DERIVATIVE; MCM 41; METHANE; PALLADIUM COMPLEX; STYRENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; GRIGNARD REACTION; PRIORITY JOURNAL;

EID: 34047265359     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.046     Document Type: Article

References (65)

1. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, New York, NY
2. In: Miyaura N. (Ed). Cross-Coupling Reactions: A Practical Guide. Topics in Current Chemistry Series 219 (2002), Springer, New York, NY
3. de Meijere A., and Diederich F. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim
4. Tamao K., Sumitani K., and Kumada M. J. Am. Chem. Soc. 94 (1972) 4374
5. Corriu R.J.P., and Masse J.P. J. Chem. Soc., Chem. Commun. (1972) 144
6. For recent reviews, see:
7. Tamao K. J. Organomet. Chem. 653 (2002) 23
8. Hillier A.C., Grasa G.A., Viciu M.S., Lee H.M., Yang C., and Nolan S.P. J. Organomet. Chem. 653 (2002) 69
9. Anctil E.J.-G., and Snieckus V. J. Organomet. Chem. 653 (2002) 150
10. Hermann W.A., Öfele K., Preysing D.V., and Schneider S.K. J. Organomet. Chem. 687 (2003) 229
11. Schröter S., Stock C., and Bach T. Tetrahedron 61 (2005) 2245
12. de Meijere A., Stulgies B., Albrecht K., Rauch K., Wegner H.A., Hopf H., Scott L.T., Eshdat L., Aprahamian I., and Rabinovitz M. Pure Appl. Chem. 78 (2006) 813
13. Banno T., Hayakawa Y., and Umeno M. J. Organomet. Chem. 653 (2002) 288
14. Lipshutz B.H., Tasler S., Chrisman W., Spliethoff B., and Tesche B. J. Org. Chem. 68 (2003) 1177
15. Frieman B.A., Taft B.R., Lee C.-T., Butler T., and Lipshutz B.H. Synthesis 17 (2005) 2989
16. Styring P., Grindon C., and Fisher C.M. Catal. Lett. 77 (2001) 219
17. Phan N.T.S., Brown D.H., Adams H., Spey S.E., and Styring P. Dalton. Trans. (2004) 1348
18. Phan N.T.S., Brown D.H., and Styring P. Green Chem. 6 (2004) 526
19. For reviews, see:
20. Corma A. Chem. Rev. 97 (1997) 2373
21. Thomas J.M. Angew. Chem., Int. Ed. 38 (1999) 3588
22. Ying J.Y., Mehnert C.P., and Wong M.S. Angew. Chem., Int. Ed. 38 (1999) 56
23. Anwander R. Chem. Mater. 13 (2001) 4419
24. Biff A., Zecca M., and Basato M. J. Mol. Catal. A: Chem. 173 (2001) 249
25. He X., and Antonelli D. Angew. Chem., Int. Ed. 41 (2002) 214
26. De Vos D.E., Dams M., Sels B.F., and Jacobs P.A. Chem. Rev. 102 (2002) 3615
27. Trong On D., Desplantier-Giscard D., Danumah C., and Kaliaguine S. Appl. Catal. A: Gen. 253 (2003) 545
28. Thomas J.M., and Raja R. J. Organomet. Chem. 689 (2004) 4110
29. Li C. Catal. Rev. 46 (2004) 419
30. Taguchi A., and Schüth F. Microporous Mesoporous Mater. 77 (2005) 1
31. Hoffmann F., Cornelius M., Morell J., and Fröba M. Angew. Chem., Int. Ed. 45 (2006) 3216
32. Mehnert C.P., Weaver D.W., and Ying J.Y. J. Am. Chem. Soc. 120 (1998) 12289
33. Zhou J., Zhou R., Mo L., Zhao S., and Zheng X. J. Mol. Catal. A: Chem. 178 (2002) 289
34. Yang H., Zhang G., Hong X., and Zhu Y. J. Mol. Catal. A: Chem. 210 (2004) 143
35. Venkatesan C., and Singh A.P. J. Catal. 227 (2004) 148
36. González-Arellano C., Corma A., Iglesias M., and Sánchez F. Adv. Synth. Catal. 346 (2004) 1758
37. Tsai F.-Y., Wu C.-L., Mou C.-Y., Chao M.-C., Lin H.-P., and Liu S.-T. Tetrahedron Lett. 45 (2004) 7503
38. Kosslick H., Mönnich I., Paetzold E., Fuhrmann H., Fricke R., Müller D., and Oehme G. Microporous Mesoporous Mater. 44-45 (2001) 537
39. Mukhopadhyay K., Sarkar B.R., and Chaudhari R.V. J. Am. Chem. Soc. 124 (2002) 9692
40. González-Arellano C., Corma A., Iglesias M., and Sánchez F. Catal. Today 107-108 (2005) 362
41. Kantam M.L., Chowdari N.S., Rahman A., and Choudary B.M. Synlett (2005) 1413
42. Bandini M., Luque R., Budarin V., and Macquarrie D.J. Tetrahedron 61 (2005) 9860
43. Cai M., Xu Q., and Wang P. J. Mol. Catal. A: Chem. 250 (2006) 199
44. Djakovitch L., Dufaud V., and Zaidi R. Adv. Synth. Catal. 348 (2006) 715
45. Clark J.H., Macquarrie D.J., and Mubofu E.B. Green Chem. 2 (2000) 53
46. Lin H.-P., and Tsai C.-P. Chem. Lett. 32 (2003) 1092
47. Chouzier S., Gruber M., and Djakovitch L. J. Mol. Catal. A: Chem. 212 (2004) 43
48. Rollet P., Kleist W., Dufaud V., and Djakovitch L. J. Mol. Catal. A: Chem. 241 (2005) 39
49. Oki A.R., and Morgan R.J. Synth. Commun. 25 (1995) 4093
50. Will G., Boschloo G., Rao S.N., and Fitzmaurice D. J. Phys. Chem. B 103 (1999) 8067
51. Doyle J.R., Slade P.E., and Jonassen H.B. Inorg. Synth. 6 (1960) 218
52. Becht J.-M., Gissot A., Wagner A., and Mioskowski C. Chem.-Eur. J. 9 (2003) 3209
53. Milstein D., and Stille J.K. J. Am. Chem. Soc. 101 (1979) 4992
54. Itoh K., Okazaki K., and Chow Y.L. Helv. Chim. Acta 87 (2004) 292
55. Mowery M.E., and DeShong P. J. Org. Chem. 64 (1999) 1684
56. Wynberg H., van Driel H., Kellogg R.M., and Buter J. J. Am. Chem. Soc. 89 (1967) 3487
57. Denmark S.E., and Ober M.H. Org. Lett. 5 (2003) 1357
58. Ohri R.V., Radosevich A.T., Hrovat K.J., Musich C., Huang D., Holman T.R., and Toste F.D. Org. Lett. 7 (2005) 2501
59. Norman R.O.C., Thomas C.B., and Willson J.S. J. Chem. Soc., Perkin Trans. 1 (1973) 325
60. Korzeniowski S.H., Blum L., and Gokel G.W. Tetrahedron Lett. 22 (1977) 1871
61. Tamura Y., Yoshimoto Y., Tada S.-I., Kunimoto K., Matsumura S., Murayama M., Shibata Y., and Enomoto H. J. Med. Chem. 24 (1981) 1006
62. Wynberg H., and Bantjes A. J. Org. Chem. 24 (1959) 1421
63. Botteghi C., Lardicci L., and Menicagli R. J. Org. Chem. 38 (1973) 2361
64. Kirsch G., and Prim D. Synth. Commun. 24 (1994) 1721
65. Eisch J.J., and Dutta S. Organometallics 24 (2005) 3355