Transition-metal-free Suzuki-type coupling reactions: Scope and limitations of the methodology

Journal of Organic Chemistry

Volumn 68, Issue 14, 2003, Pages 5660-5667

  Leadbeater, Nicholas E ^a   Marco, Maria ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTIONS;

CATALYSTS; MICROWAVES; PHASE TRANSITIONS; TRANSITION METALS;

AROMATIC HYDROCARBONS;

BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; HALIDE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0037999827     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034230i     Document Type: Article

References (55)

1. (a) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
2. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
3. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
4. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
5. See for example: Ennis, D. S.; McManus, J.; Wood-Kaczmar, W.; Richardson, J.; Smith, G. E.; Carstairs, A. Org. Proc. Res. Dev. 1999, 3, 248.
6. For a general introduction to organic synthesis in water see: (a) Organic synthesis in water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, UK, 1998. (b) Li, C.-J.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: Dordrecht, The Netherlands, 1997.
7. For a general introduction to organic synthesis in water see: (a) Organic synthesis in water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, UK, 1998. (b) Li, C.-J.; Chen, T.-H. Organic Reactions in Aqueous Media; Wiley: Dordrecht, The Netherlands, 1997.
8. For an introduction to the use of organometallic catalysts in aqueous-phase catalysis see: Aqueous-Phase Organometallic Catalysis, Concepts and Applications; Cornils, B., Herrmann, W. A., Eds; Wiley-VCH: Weinheim, Germany, 1998.
9. Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437.
10. Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721.
11. Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384.
12. Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.
13. Botella, L.; Nájera, C. Angew. Chem., Int. Ed. Engl. 2002, 41, 179.
14. Castanet, A.-S.; Colobert, F.; Desmurs, J.-R.; Schlama, S. J. Mol. Catal. 2002, 182-183, 481.
15. For reviews on the area see: (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (c) Lindström, P.; Tierney, J.; Wathey B.; Westman, J. Tetrahedron 2001, 57, 9225. (d) Perreux L.; Loupy, A. Tetrahedron 2001, 57, 9199. (e) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851.
16. For reviews on the area see: (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (c) Lindström, P.; Tierney, J.; Wathey B.; Westman, J. Tetrahedron 2001, 57, 9225. (d) Perreux L.; Loupy, A. Tetrahedron 2001, 57, 9199. (e) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851.
17. For reviews on the area see: (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (c) Lindström, P.; Tierney, J.; Wathey B.; Westman, J. Tetrahedron 2001, 57, 9225. (d) Perreux L.; Loupy, A. Tetrahedron 2001, 57, 9199. (e) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851.
18. For reviews on the area see: (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (c) Lindström, P.; Tierney, J.; Wathey B.; Westman, J. Tetrahedron 2001, 57, 9225. (d) Perreux L.; Loupy, A. Tetrahedron 2001, 57, 9199. (e) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851.
19. For reviews on the area see: (a) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (c) Lindström, P.; Tierney, J.; Wathey B.; Westman, J. Tetrahedron 2001, 57, 9225. (d) Perreux L.; Loupy, A. Tetrahedron 2001, 57, 9199. (e) Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851.
20. For reviews on the concepts see: (a) Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213. (b) Mingos, D. M. P. Chem. Soc. Rev. 1991, 20, 1.
21. For reviews on the concepts see: (a) Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213. (b) Mingos, D. M. P. Chem. Soc. Rev. 1991, 20, 1.
22. Gedye, R.; Smith, F.; Westaway, K.; Humera, A.; Baldisera, L.; Laberge, L.; Rousell, L. Tetrahedron Lett. 1986, 27, 279.
23. Giguere, R.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945.
24. For some recent examples see: (a) Westman, J. Org. Lett. 2001, 3, 3745. (b) Kuhnert, N.; Danks, T. N. Green Chem. 2001, 3, 98. (c) Loupy, A.; Regnier, S. Tetrahedron Lett. 1999, 40, 6221. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
25. For some recent examples see: (a) Westman, J. Org. Lett. 2001, 3, 3745. (b) Kuhnert, N.; Danks, T. N. Green Chem. 2001, 3, 98. (c) Loupy, A.; Regnier, S. Tetrahedron Lett. 1999, 40, 6221. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
26. For some recent examples see: (a) Westman, J. Org. Lett. 2001, 3, 3745. (b) Kuhnert, N.; Danks, T. N. Green Chem. 2001, 3, 98. (c) Loupy, A.; Regnier, S. Tetrahedron Lett. 1999, 40, 6221. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
27. For some recent examples see: (a) Westman, J. Org. Lett. 2001, 3, 3745. (b) Kuhnert, N.; Danks, T. N. Green Chem. 2001, 3, 98. (c) Loupy, A.; Regnier, S. Tetrahedron Lett. 1999, 40, 6221. (d) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
28. Stadler, A.; Kappe, A. C. Eur. J. Org. Chem. 2001, 919.
29. Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973.
30. Leadbeater, N. E.; Marco, M. J. Org. Chem. 2002, 68, 888.
31. Leadbeater, N. E.; Marco, M. Angew. Chem., Int. Ed. Engl. 2003, 42, 1407.
32. (a) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. A. Angew. Chem., Int. Ed. Engl. 2002, 41, 4120.
33. (b) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540.
34. (a) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127.
35. (b) Brase, S.; Dahmen, S.; Lauterwasser, F.; Leadbeater, N. E.; Sharp, E. L. Bioorg. Med. Chem. Lett. 2002, 12, 1849.
36. (c) Heidenreich, R. G.; Kohler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118.
37. (d) Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. Engl. 2001, 40, 3469.
38. This competitive deboronation of boronic acids in basic aqueous media has been reported on a number of occasions. For a study of the reaction see: (a) Kuvila, H. G.; Reuwer, J. F.; Mangravite, J. A. J. Am. Chem. Soc. 1964, 86, 2666. (b) Kuvila, H. G.; Nahabedian, K. V. J. Am. Chem. Soc. 1961, 83, 2159.
39. This competitive deboronation of boronic acids in basic aqueous media has been reported on a number of occasions. For a study of the reaction see: (a) Kuvila, H. G.; Reuwer, J. F.; Mangravite, J. A. J. Am. Chem. Soc. 1964, 86, 2666. (b) Kuvila, H. G.; Nahabedian, K. V. J. Am. Chem. Soc. 1961, 83, 2159.
40. (a) Zim, D.; Monteiro, A. L. Tetrahedron Lett. 2002, 43, 4009.
41. (b) Griffiths, C.; Leadbeater, N. E. Tetrahedron Lett. 2000, 41, 2487.
42. (c) Lipshutz, B. H.; Sclafani, J. A.; Blomgren, P. A. Tetrahedron 2000, 56, 2139.
43. (d) Leadbeater, N. E.; Resouly, S. M. Tetrahedron 1999, 55, 11889.
44. Bedford, R. B.; Hazelwood, S. L.; Albisson, D. A. Organometallics 2002, 21, 2599.
45. Thathagar, M. B.; Beckers, J.; Rothenberg, G. J. Am. Chem. Soc. 2002, 124, 2159.
46. (a) Liu, X. X.; Deng, M. Z. Chem. Commun. 2002, 622.
47. (b) Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3, 2149.
48. For a review see: Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
49. Zim, D.; Monteiro, A. L.; Dupont, J. Tetrahedron Lett. 2000, 41, 8199.
50. For a review see: Luh, T. Y.; Leung, M. K.; Wong, K. T. Chem. Rev. 2000, 100, 3187.
51. (a) Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
52. (b) Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 2002, 41, 3910.
53. (c) Kirchhoff, J. H.; Dai, C. Y.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 2002, 41, 1945.
54. (d) Soderquist, J. A.; Leon, G.; Colberg, J. C.; Martinez, I. Tetrahedron Lett. 1995, 36, 3119.
55. Villemin, D.; Gómez-Escalonilla M. J.; Saint-Clair, J.-F. Tetrahedron Lett. 1996, 37, 8219.