Biphasic Suzuki coupling reactions of aryl or benzyl bromides employing cobalt-containing phosphine ligand coordinated palladium complex

Tetrahedron

Volumn 61, Issue 15, 2005, Pages 3835-3839

  Chang, Chin Pei ^a   Huang, Yi Luen ^a   Hong, Fung E ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

Biphasic Suzuki reaction; Cobalt containing phosphine; Palladium complex; Phase transfer agent

Indexed keywords

BENZYL BROMIDE; COBALT; PALLADIUM; PHOSPHINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHELATION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; PHASE TRANSITION; PRIORITY JOURNAL; REACTION TIME; SUZUKI REACTION; TEMPERATURE DEPENDENCE;

LATEOLABRAX JAPONICUS;

EID: 15044354720     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.134     Document Type: Article

References (54)

1. A. Suzuki J. Organomet. Chem. 576 1999 147 168 and references therein
2. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483 and references therein
3. A. Suzuki F. Diederich P.J. Stang Metal-Catalyzed Cross-Coupling Reactions 1988 Wiley-VCH Weinheim
4. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633 9695
5. S.P. Stanforth Tetrahedron 54 1998 263 303
6. N. Miyaura, and A. Suzuki L.S. Liebeskind Advances in Metal-Organic Chemistry Vol. 6 1998 JAI London 187
7. O. Navarro, R.A. Kelly III, and S.P. Nolan J. Am. Chem. Soc. 125 2003 16194 16195
8. M.S. Viciu, R.A. Kelly III, E.D. Stevens, F. Naud, M. Studer, and S.P. Nolan Org. Lett. 5 2003 1479 1482
9. J. Yin, M.P. Rainka, X.X. Zhang, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 1162 1163
10. J.P. Stambuli, R. Kuwano, and J.F. Hartwig Angew. Chem. Int. Ed. 41 2002 4746 4748
11. S.R. Chemler, D. Trauner, and S.J. Danishefsky Angew. Chem. Int. Ed. 40 2001 4544 4568
12. J.P. Wolfe, H. Tomori, J.P. Sadighi, J. Yin, and S.L. Buchwald J. Org. Chem. 65 2000 1158 1174
13. J.P. Wolfe, and S.L. Buchwald Angew. Chem. Int. Ed. 38 1999 2413 2416
14. J.P. Wolfe, R.A. Singer, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9550 9561
15. X. Bei, T. Crevier, A.S. Guram, B. Jandeleit, T.S. Powers, H.W. Turner, T. Uno, and W.H. Weinberg Tetrahedron Lett. 40 1999 3855 3870
16. A.F. Littke, and G.C. Fu Angew. Chem. Int. Ed. 37 1998 3387 3388
17. For selected examples, see: (a) M. Miyaura Angew. Chem. Int. Ed. 43 2004 2201 2203
18. D.W. Old, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 9722 9723
19. X. Bei, H.W. Turner, W.H. Weinberg, A.S. Guram, and J.L. Petersen J. Org. Chem. 64 1999 6797 6803
20. A.F. Littke, and G.C. Fu J. Am. Chem. Soc. 123 2001 6989 7000
21. M.G. Andreu, A. Zapf, and M. Beller Chem. Commun. 2000 2475 2476
22. R.B. Bedford, and C.S.J. Cazin Chem. Commun. 2001 1540 1541
23. A. Schnyder, A.F. Indolese, M. Studer, and H.U. Blaser Angew. Chem. Int. Ed. 41 2002 3668 3671
24. General reviews, see (a) O. Delacroix, and J.A. Gladysz Chem. Commun. 2003 665 675
25. A. Salzer Coord. Chem. Rev. 242 2003 59
26. J.G. Planas, and J.A. Gladysz Inorg. Chem. 41 2002 6947 6949
27. Q.-S. Hu, Y. Lu, Z.-Y. Tang, and H.-B. Yu J. Am. Chem. Soc. 125 2003 2856 2857
28. G. Mann, and G.F. Hartwig J. Am. Chem. Soc. 118 1996 13109 13110
29. T.E. Pickett, F.X. Roca, and C.J. Richards J. Org. Chem. 68 2003 2592 2599
30. N. Kataoka, Q. Shelby, J.P. Stambuli, and J.F. Hartwig J. Org. Chem. 67 2002 5553 5566
31. Z.-Y. Tang, Y. Lu, and Q.-S. Hu Org. Lett. 5 2003 297 300
32. J.F. Jesen, and M. Johannsen Org. Lett. 5 2003 3025 3028
33. T.J. Colacot, and H.A. Shea Org. Lett. 6 2004 3731 3734
34. F.-E. Hong, Y.-C. Chang, R.-E. Chang, S.-C. Chen, and B.-T. Ko Organometallics 21 2002 961 967
35. F.E. Hong, Y.C. Chang, C.P. Chang, and Y.L. Huang Dalton Trans. 2004 157 165
36. J. Zhou, and G.C. Fu J. Am. Chem. Soc. 126 2004 1340 1341
37. G.A. Molander, B.W. Katona, and F. Machrouhi J. Org. Chem. 67 2002 8416 8423
38. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, and K. Hirotsu J. Org. Chem. 106 1984 158
39. See: B. Cornils W.A. Herrmann Aqueous-Phase Organometallic Catalysis: Concepts and Applications 1998 Wiley-VCH Weinheim, Germany
40. For recent examples, see: (a) H. Gulyas, A. Szollosy, B.E. Hanson, and J. Bakos Tetrahedron Lett. 43 2002 2543 2546
41. D.J. Brauer, M. Hingst, K.W. Kottsieper, C. Like, T. Nickel, M. Tepper, O. Stelzer, and W.S. Sheldrick J. Organomet. Chem. 645 2002 14 26
42. N.E. Leadbeater, and M. Marco J. Org. Chem. 68 2003 5660 5667
43. L. Botella, and C. Nájera Angew. Chem. Int. Ed. Engl. 41 2002 179 181
44. A.-S. Castanet, F. Colobert, J.-R. Desmurs, and S.J. Schlama J. Mol. Catal. 182-183 2002 481
45. T.-Y. Luh, M.-K. Leung, and K.-T. Wong Chem. Rev. 100 2000 3187 3204
46. D.J. Cárdenas Angew. Chem. Int. Ed. 38 1999 3018 3020
47. 3 couplings of primary alkyl iodides and organozinc reagents: (c) A. Devasagayaraj, T. Stüdemann, and P. Knochel Angew. Chem. Int. Ed. Engl. 34 1995 2723 2725
48. R. Giovannini, T. Stüdemann, G. Dussin, and P. Knochel Angew. Chem. Int. Ed 37 1998 2387 2390
49. R. Giovannini, T. Stüdemann, A. Devasagayaraj, G. Dussin, and P. Knochel J. Org. Chem. 64 1999 3544 3553
50. J.K. Stille F.R. Hartley S. Patai The Chemistry of the Metal-Carbon Bond Vol. 2 1985 Wiley New York 625 Chapter 9
51. T. Ishiyama, N. Miyaura, and A. Suzuki Tetrahedron Lett. 32 1991 6923 6926
52. A. Goliaszewski, and J. Schwartz Tetrahedron 41 1985 5779 5789
53. J.P. Wolfe, and S.L. Buchwald Angew. Chem. Int. Ed. 38 1999 2413 2416
54. J.P. Wolfe, R.A. Singer, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 9550 9561