Suzuki coupling reactions in neat water as the solvent: Where in the biphasic reaction mixture do the catalytic reaction steps occur?

Chemistry - A European Journal

Volumn 18, Issue 48, 2012, Pages 15485-15494

  Röhlich, Christoph ^a   Wirth, Andreas S ^a   Köhler, Klaus ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

biphasic catalysis; C C coupling; palladium; Suzuki reaction; water

Indexed keywords

AQUEOUS LAYER; BIPHASIC CATALYSIS; BIPHASIC REACTION; BROMOARENES; C-C COUPLING; CATALYTIC PROCESS; CATALYTIC REACTIONS; COUPLING REACTION; HYDROPHOBIC SUBSTRATE; ORGANIC LAYERS; PALLADIUM CATALYST; PD SPECIES; PRECATALYSTS; PURE WATER; REACTION PARAMETERS; SIDE PRODUCTS; STIRRING RATES; SUZUKI COUPLING REACTION; SUZUKI COUPLINGS; SUZUKI REACTION; SYSTEMATIC VARIATION; TWO LIQUID PHASIS; VARIATION OF PARAMETERS; WATER PHASE;

CATALYSIS; CATALYST ACTIVITY; EXPERIMENTS; PALLADIUM; WATER;

MIXTURES;

EID: 84869392567     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201266     Document Type: Article

References (60)

1. A. Chanda, V. V. Fokin, Chem. Rev. 2009, 109, 725.
2. M. C. Pirrung, Chem. Eur. J. 2006, 12, 1312.
3. Y. Jung, R. A. Marcus, J. Am. Chem. Soc. 2007, 129, 5492.
4. B. M. Trost, E. J. McEachern, J. Am. Chem. Soc. 1999, 121, 8649.
5. F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron 2008, 64, 3047.
6. K. H. Shaughnessy, Chem. Rev. 2009, 109, 643.
7. M. R. an der Heiden, H. Plenio, Chem. Eur. J. 2004, 10, 1789
8. A. M. Trzeciak, E. Mieczynska, J. J. ZiÃlkowski, W. Bukowski, A. Bukowska, J. Noworolb, J. Okalc, New J. Chem. 2008, 32, 1124
9. R. B. Bedford, M. E. Blake, C. P. Butts, D. Holder, Chem. Commun. 2003, 466
10. C. Fleckenstein, H. Plenio, Chem. Eur. J. 2008, 14, 4267
11. C. Fleckenstein, H. Plenio, Chem. Soc. Rev. 2010, 39, 694.
12. C. Fleckenstein, S. Roy, S. Leuthäuaßer, H. Plenio, Chem. Commun. 2007, 2870.
13. H. Li, Y. Wu, Appl. Organomet. Chem. 2008, 22, 233
14. D.-H. Lee, Y. H. Lee, D. I. Kim, Y. Kim, W. T. Lim, J. M. Harrowfield, P. Thuéry, M.-J. Jin, Y. C. Park, I.-M. Lee, Tetrahedron 2008, 64, 7178
15. E. J. García Suárez, A. Ruiz, S. Castillõn, W. Oberhauser, C. Bianchini, C. Claver, Dalton Trans. 2007, 2859
16. B. Inés, R. SanMartin, M. J. Moure, E. Domínguez, Adv. Synth. Catal. 2009, 351, 2124
17. I. D. Kostas, A. G. Coutsolelos, G. Charalambidis, A. Skondra, Tetrahedron Lett. 2007, 48, 6688.
18. P. Conelly-Espinosa, D. Morales-Morales, Inorg. Chim. Acta 2010, 363, 1311.
19. K. Yu, W. Sommer, J. M. Richardson, M. Weck, C. W. Jones, Adv. Synth. Catal. 2005, 347, 161
20. N. Phan, M. van der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609
21. I. P. Beletskaya, A. V. Cheprakov, J. Organomet. Chem. 2004, 689, 4055
22. M. Weck, C. W. Jones, Inorg. Chem. 2007, 46, 1865
23. V. Farina, Adv. Synth. Catal. 2004, 346, 1553.
24. C. Röhlich, K. Köhler, Adv. Synth. Catal. 2010, 352, 2263.
25. G. Wei, W. Zhang, F. Wen, Y. Wang, M. Zhang, J. Phys. Chem. C 2008, 112, 10827
26. Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Org. Lett. 2002, 4, 3371
27. P. Zheng, W. Zhang, J. Catal. 2007, 250, 324.
28. B. H. Lipshutz, B. R. Taft, Org. Lett. 2008, 10, 1329
29. B. H. Lipshutz, A. R. Abela, Org. Lett. 2008, 10, 5329
30. J. Pschierer, H. Plenio, Eur. J. Org. Chem. 2010, 2934.
31. D. Schönfelder, O. Nuyken, R. Weberskirch, J. Organomet. Chem. 2005, 690, 4648
32. M. Meise, R. Haag, ChemSusChem 2008, 1, 637
33. S. Sawoo, D. Srinami, P. Dutta, R. Lahiri, A. Sarkar, Tetrahedron 2009, 65, 4367.
34. Q. Yang, S. Ma, J. Li, F. Xiao, H. Xiong, Chem. Commun. 2006, 2495.
35. M. Lysén, K. Köhler, Synlett 2005, 1671.
36. M. Lysén, K. Köhler, Synthesis 2006, 692.
37. M. Moreno-Mañas, M. Pérez, R. Pleixats, J. Org. Chem. 1996, 61, 2346.
38. C. Röhlich, K. Köhler, unpublished results.
39. S. S. Soomro, C. Röhlich, K. Köhler, Adv. Synth. Catal. 2011, 353, 767.
40. G. E. K. Branch, D. L. Yabroff, B. Bettman, J. Am. Chem. Soc. 1934, 56, 937.
41. G. Graziano, J. Chem. Phys. 2004, 121, 1878.
42. V. CalÃ, A. Nacci, A. Monopoli, Eur. J. Org. Chem. 2006, 3791.
43. M. T. Reetz, E. Westermann, Angew. Chem. 2000, 112, 170
44. Angew. Chem. Int. Ed. 2000, 39, 165.
45. V. CalÃ, A. Nacci, A. Monopoli, A. Fornaro, L. Sabbatini, N. Cioffi, N. Ditaranto, Organometallics 2004, 23, 5154.
46. D. Astruc, Inorg. Chem. 2007, 46, 1884
47. D. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem. 2005, 117, 8062
48. Angew. Chem. Int. Ed. 2005, 44, 7852
49. A. Khadri Diallo, C. Ornelas, L. Salmon, J. Ruiz Aranzaes, D. Astruc, Angew. Chem. 2007, 119, 8798
50. Angew. Chem. Int. Ed. 2007, 46, 8644.
51. S. S. Soomro, F. L. Ansari, K. Chatziapostolou, K. Köhler, J. Catal. 2010, 273, 138.
52. A. F. Schmidt, A. Al Halaiqa, V. V. Smirnov, Synlett 2006, 2861.
53. J. G. de Vries, Dalton Trans. 2006, 421.
54. I. Pryjomska-Raya, A. Gnieweka, A. M. Trzeciaka, J. J. ZiÃłkowskia, W. Tylus, Top. Catal. 2006, 40, 173.
55. S.-H. Huang, J.-R. Chen, F.-Y. Tsai, Molecules 2010, 15, 315
56. D. Badone, M. Baroni, R. Cardamone, A. Ielmini, U. Guzzi, J. Org. Chem. 1997, 62, 7170.
57. B. J. Gallon, R. W. Kojima, R. B. Kraner, P. L. Diaconescu, Angew. Chem. 2007, 119, 7389
58. Angew. Chem. Int. Ed. 2007, 46, 7251.
59. N. E. Leadbeater, Chem. Commun. 2005, 2881.
60. L. Liu, Y. Zhang, Y. Wang, J. Org. Chem. 2005, 70, 6122.