Review on green chemistry - Suzuki cross coupling in aqueous media

Canadian Journal of Chemistry

Volumn 83, Issue 3, 2005, Pages 266-272

  Franzén, Robert ^a   Xu, Youjun ^b  

^a TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Aqueous synthesis media; Green chemistry; Metal catalyzed cross coupling reactions; Suzuki reaction

Indexed keywords

CARBON; CHEMICAL BONDS; MOLECULES; NETWORK PROTOCOLS;

CARBON-CARBON BONDS; LIGANDS; SUZUKI CROSS COUPLING;

SOLUTIONS;

LIGAND; ORGANIC SOLVENT;

AQUEOUS SOLUTION; CHEMICAL BOND; REACTION ANALYSIS; RELIABILITY; SHORT SURVEY; SUZUKI REACTION; SYNTHESIS; TECHNIQUE;

EID: 20044378683     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-048     Document Type: Short Survey

References (67)

1. P.T. Anastas, L.G. Heine, and T.C. Williamson. Green chemical syntheses and processes. American Chemical Society, Washington, D.C. 2000.
2. C.-J. Li and T.-H. Chan. Organic reactions in aqueous media. John Wiley and Sons Inc., New York. 1997.
3. J.M. Davidson and C.J. Triggs. J. Chem. Soc. A, 6, 1324 (1968).
4. K. Carves. J. Org. Chem. 43, 2870 (1978).
5. N. Miyaura and A. Suzuki. J. Chem. Soc. Chem. Commun. 866 (1979).
6. N. Miyaura and A. Suzuki. Chem. Rev. 95, 2457 (1995).
7. R. Franzén. Can. J. Chem. 78, 957 (2000).
8. R.F. Heck. Org. React. 27, 345 (1982).
9. T. Hayashi and M. Kumada. Acc. Chem. Res. 15, 395 (1982).
10. J.W. Labadie, D. Tueting, and S.K. Stille. J. Org. Chem. 48, 4634 (1983).
11. E.-I. Negishi. Acc. Chem. Res. 15, 340 (1982).
12. K. Sonogashira. J. Organomet. Chem. 653, 46 (2002).
13. J. Tsuji. Transition metal reagents and catalysts: Innovations in organic synthesis. John Wiley and Sons, New York. 2002.
14. F. Lipton, M.A. Mauragis, M.T. Maloney, M.F. Veley, D.W. VanderBor, J.J. Newby, R.B. Appell, and E.D. Daugs. Org. Process Res. Dev. 7, 385 (2003).
15. M. Beller and A. Zapf. In Handbook of organopalladium chemistry for organic synthesis. Edited by E. Negishi. Wiley, Hoboken, New Jersey. Vol. 1. 2002. p. 1209.
16. D.S. Ennis, J. McManus, W. Wood-Kaczmar, J. Richardson, G.E. Smith, and A. Carstairs. Org. Process Res. Dev. 3, 248 (1999).
17. Y. Mori, M. Nakamura, T. Wakabayashi, K. Mori, and S. Kobayashi. Synlett, 4, 601 (2002).
18. A. Herrmann and C.W. Kohlpaintner. Angew. Chem. Int. Ed. Engl. 32, 1524 (1993).
19. (a) U.M. Lindström. Chem. Rev. 102, 2751 (2002);
20. (b) R. Kolodziuk, A. Penciu, M. Tollabi, E. Framery, C. Goux-Henry, A. Iourtchenko, and D. Sinou. J. Organomet. Chem. 687, 384 (2003);
21. (c) S. Parisot, R. Kolodziuk, C. Goux-Henry, A. Iourtchenko, and D. Sinou. Tetrahedron Lett. 43, 7397 (2002);
22. M. Bellar, J.G.E. Krauter, and A. Zapf. Angew. Chem. Int. Ed. Engl. 36, 772 (1997).
23. J. Zhang and C.-G. Xia. J. Mol. Catalysis A, 206, 59 (2003).
24. T. Vincent and E. Guibal. Ind. Eng. Chem. Res. 41, 5158 (2002).
25. F. Quignard, A. Choplin, and A. Domard. Langmuir, 16, 9106 (2000).
26. M.-A. Yin, G.-L. Yuan, Y-Q. Wu, M.-Y. Huang, and Y-Y Jiang. J. Mol. Catalysis, 147, 93 (1999).
27. J.J.E. Hardy, S. Hubert, D.C. Macquarrie, and A.J. Wilson. Green Chem. 6, 53 (2004).
28. D.E. De Vos, I.F.J. Vankelecom, and P.A. Jacobs. Chiral catalyst immobilization and recycling. Wiley-VCH, Weinheim. 2000.
29. W. Gu, W.-J. Zhou, and D.L. Gin. Chem. Mater. 13, 1949 (2001).
30. J. Jamis, J.R. Anderson, R.S. Dickson, E.M. Campi, and W.R. Jackson. J. Organomet. Chem. 603, 80 (2000).
31. G. Sartori, F. Bigi, R. Maggi, A. Mazzacani, and G. Oppici. Eur. J. Org. Chem. 2513 (2001).
32. (a) C.R. LeBlond, A.T. Andrews, Y. Sun, and J.R. Sowa, Jr. Org. Lett. 3, 1555 (2001);
33. (b) H. Sakurai, T. Tsukuda, and T. Hirao. J. Org. Chem. 67, 2721 (2002);
34. (c) T. Tagata and M. Nishida. J. Org. Chem. 68, 9412 (2003);
35. (d) D.A. Conlon, B. Pipik, S. Ferdinand, C.R. LeBlond, J.R. Sowa, B. Izzo, P. Collins, G.J. Ho, J.M. Williams, Y.J. Shi, and Y. Sun. Adv. Synth. Catal. 345, 931 (2003).
36. M.T. Reetz and E. Westermann. Angew. Chem. 112, 170 (2000).
37. G.W. Kabalka, V. Namboodiri, and L. Wang. J. Chem. Soc. Chem. Commun. 775 (2001).
38. S.P. Stanforth. Tetrahedron, 54, 263 (1998).
39. F. Ullmann. Ber. 36, 2389 (1903).
40. J.J. Li and G.W. Gribble. Palladium in heterocyclic chemistry. Pergamon, New York. 2000.
41. C.N. Johnson, G. Stemp, N. Anand, S.C. Stephen, and T. Gallagher. Synlett, 1025 (1998).
42. (a) R.J. Sundberg. Indoles. Academic Press, London. 1996;
43. (b) Y. Yang and A.R. Martin. Heterocycles, 34, 1395 (1992).
44. A. Zoltewicz and M.P. Cruskie, Jr. Tetrahedron, 51, 11393 (1995).
45. J. Li and W.S. Yue. Tetrahedron Lett. 40, 4507 (1999).
46. T. Soos, G. Timari, and G. Hajos. Tetrahedron Lett. 40, 8607 (1999).
47. (a) U. Wellmar, A.-B. Hörnfeldt, and S. Gronowitz. J. Heterocycl. Chem. 32, 1159 (1995);
48. (b) S.L. Hargreaves, B.L. Pilkington, S.E. Russell, and P.A. Worthington. Tetrahedron Lett. 41, 1653 (2000).
49. D. Wang and J. Haseltine. J. Heterocycl. Chem. 31, 1637 (1994).
50. (a) D. Peters, A.-B. Hörnfeldt, and T. Musil. J. Heterocycl. Chem. 27, 2165 (1990);
51. (b) A.L. Casalnuovo and J.C. Calabrese. J. Am. Chem. Soc. 112, 4324 (1990).
52. R. Franzén and J. Tois. Comb. Chem. High Throughput Scr. 6, 433 (2003).
53. T.I. Wallow and B.M. Novak. J. Am. Chem. Soc. 113, 7411 (1991).
54. S. Martina and A.-D. Schluter. Macromolecules, 25, 3607 (1992).
55. X. Zhou, Z. Zhou, T.C.W. Mak, and K.S. Chan. J. Chem. Soc. Perkin Trans. 1, 2519 (1994).
56. R. Suau, R. Rico, F. Najera, F.J. Ortiz-Lopez, J.M. Lopez-Romero, M. Moreno-Manas, and A. Roglans. Tetrahedron, 60, 5725 (2004)
57. G.A. Molander and F. Dehmel. J. Am. Chem. Soc. 126, 10 313 (2004).
58. P.J. Mohr and R.L. Halcomb. J. Am. Chem. Soc. 125, 1712 (2003).
59. C. Tsukano and M. Sasaki. J. Am. Chem. Soc. 125, 14 294 (2003).
60. A. Bouillon, A.S. Voisin, A. Robic, J.-C. Lancelot, V. Collot, and S. Rault. J. Org. Chem. 68, 10 178 (2003).
61. B.M. Crowley, Y. Mori, C.C. McComas, D. Tang, and D.L. Boger. 126, 4310 (2004)
62. K.C. Nicolaou and E.J. Sorensen. Classics in total synthesis. VCH Verlagsgesellschaft mbH, Weinheim. 1996.
63. N.G. Andersen, S.P. Maddaford, and B.A. Keay. J. Org. Chem. 61, 9556 (1996).
64. J. Yin and S.L. Buchwald. J. Am. Chem. Soc. 122, 12051 (2000).
65. A.N. Cammidge and K.V.L. Crepy. Chem. Commun. 1723 (2000).
66. A.-S. Castanet, F. Colobert, P.-E. Broutin, and M. Obringer. Tetrahedron: Asymmetry, 13, 659 (2002).
67. A. Herrbach, A. Marinetti, O. Baudoin, D. Guenard, and F. Gueritte. J. Org. Chem. 68, 4897 (2003).