Radical catalysis of kumada cross-coupling reactions using functionalized grignard reagents

Angewandte Chemie - International Edition

Volumn 48, Issue 1, 2009, Pages 205-209

  Manolikakes, Georg ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cross coupling; Homogeneous catalysis; Organomagnesium compounds; Palladium; Radicals

Indexed keywords

BROMINE COMPOUNDS; CATALYSIS; CHEMICAL BONDS; CHEMICAL REACTIONS; MAGNESIUM COMPOUNDS; REACTION KINETICS;

ALKYL IODIDES; ARYL BROMIDES; CHEMICAL EQUATIONS; CROSS-COUPLING; FUNCTIONALIZED; GRIGNARD REAGENTS; HOMOGENEOUS CATALYSIS; ORGANOMAGNESIUM COMPOUNDS; PALLADIUM CATALYSTS; RADICAL PATHWAYS; RADICALS;

PALLADIUM;

EID: 58249098579     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803730     Document Type: Article

References (60)

1. a) R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144;
2. b) K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374.
3. For recent selected publications on Kumada reactions, see: a) N. Yoshikai, H. Mashima, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 17978;
4. b) M. E. Limmert, A. H. Roy, J. F. Hartwig, J. Org. Chem. 2005, 70, 9364;
5. c) L. Ackermann, R. Born, J. H. Spatz, P. Meyer, Angew. Chem. 2005, 117, 7382;
6. Angew. Chem. Int. Ed. 2005, 44, 7216;
7. d) J. Huang, S. P. Nolan, J. Am. Chem. Soc. 1999, 121, 9889;
8. e) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayer, W. A. Herrmann, Angew. Chem. 2000, 112, 1672;
9. Angew. Chem. Int. Ed. 2000, 39, 1602.
10. B. M. Trost, Science 1991, 254, 1471.
11. a) F. Diederich, P. J. Stang Eds. , Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 1998;
12. b) J. Tsuji, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, UK, 1995;.
13. a) J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Commun. 2007, 825;
14. b) J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646;
15. c) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222.
16. a) D. W. Old, J. P. Wolfe, S. L Buchwald, J. Am. Chem. Soc. 1998, 120, 9722;
17. b) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550.
18. R. Martin, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3844.
19. For some examples of Kumada couplings at low temperatures see: a) M. G. Organ, M. Abdel-Hadi, S. Avola, N. Hadei, J. Nasielski, C. J. O'Brien, C. Valente, Chem. Eur. J. 2007, 13, 150;
20. b) V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner, P. Knochel, Tetrahedron 2002, 58, 4429;
21. c) V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner, P. Knochel, Tetrahedron Lett. 2001, 45, 5717.
22. F. Piller, P. Appukkuttan, A. Gavryushin, M. Helm, P. Knochel, Angew. Chem. 2008, 120, 6907;
23. Angew. Chem. Int. Ed. 2008, 47, 6802.
24. a) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907;
25. Angew. Chem. Int. Ed. 2004, 43, 1871;
26. b) T. E. Barder, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 5096;
27. c) M. R. Biscoe, T. E. Barder, S. L. Buchwald, Angew. Chem. 2007, 119, 7370;
28. Angew. Chem. Int. Ed. 2007, 46, 7232.
29. a) M. G. Organ, M. Abdel-Hadi, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, M. Sayah, C. Valente, Chem. Eur. J. 2008, 14, 2443;
30. b) M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 4749;
31. c) N. Hadei, E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, J. Org. Chem. 2005, 70, 8503.
32. a) A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396;
33. Angew. Chem. Int. Ed. 2004, 43, 3333;
34. b) P. Knochel, W. Dohle, N. Gommermann, F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. 2003, 115, 4438;
35. Angew. Chem. Int. Ed. 2003, 42, 4302.
36. After 1 h of reaction time the organomagnesium compound was completly consumed as a result of enolization and addition to the keto function.
37. The addition of the alkyl iodide after the preparation of the Grignard reagent had the same effect. See the Supporting Information for further details.
38. Catalytic amounts of the alkyl iodide resulted in the decomposition of the catalyst prior to complete consumption of the starting aryl bromide.
39. The arylmagnesium reagent 1c is only stable below -20°C and decomposes at 25°C within 10 min.
40. As no general rule could be found for the selection of the best Pd catalyst, each reaction was tested with both catalyst systems.
41. Under the conditions described by Buchwald et al. (low temperature, THF/toluene) similar yields and reaction times were obtained (see Ref. [7] for details). However, when the reaction was performed at 25°C in THF/toluene, several by-products were obtained (typically <5% by GC-MS analysis) that arose from radical reactions of toluene.
42. a) E. J. Corey, M. F. Semmelhack, L. S. Hegedus, J. Am. Chem. Soc. 1968, 90, 2416;
43. b) E. J. Corey, M. F. Semmelhack, L. S. Hegedus, J. Am. Chem. Soc. 1968, 90, 2417;
44. c) L. S. Hegedus, E. L. Waterman, J. Am. Chem. Soc. 1974, 96, 6789;
45. d) L. S. Hegedus, L. L. Miller, J. Am. Chem. Soc. 1975, 97, 459;
46. e) L. S. Hegedus, D. H. P. Thompson, J. Am. Chem. Soc. 1985, 107, 5663;
47. f) I. H. Elson, D. G. Morrell, J. K. Kochi, J. Organomet. Chem. 1975, 84, C7;
48. g) T. T. Tsou, J. K. Kochi, J. Am. Chem. Soc. 1979, 101, 6319;
49. h) T. T. Tsou, J. K. Kochi, J. Am. Chem. Soc. 1979, 101, 7547;
50. i) J. A. Labinger, A. V. Kramer, J. A. Osborn, J. Am. Chem. Soc. 1973, 95, 7908;
51. j) A. V. Kramer, J. A. Labinger, J. S. Bradley, J. A. Osborn, J. Am. Chem. Soc. 1974, 96, 7145;
52. k) A. V. Kramer, J. A. Osborn, J. Am. Chem. Soc. 1974, 96, 7832.
53. For an overview of reactions of metal complexes with organic halides, see: a) J. K. Kochi, Organometallic Mechanisms and Catalysis, Academic Press, New York, 1978;
54. b) D. Astruc, Electron Transfer and Radical Processes in Transition-Metal Chemistry, Wiley-VCH, New York, 1995.
55. The ratio of the obtained products does not change upon addition of an extra iodine source (TBAI or LiI) or when the reaction is performed with the organomagnesium reagent 1g, prepared by magnesium insertion into the corresponding aryl iodide.
56. a) D. P. Curran, C.-T. Chang, Tetrahedron Lett. 1990, 31, 933;
57. b) T. Ishiyama, S. Abe, N. Miyaura, A. Suzuki, Chem. Lett. 1992, 691;
58. c) H. Stadtmüller,A. Vaupel, C. E. Tucker, T. Stüdemann, P. Knochel, Chem. Eur. J. 1996, 2, 1204;
59. d) H. Stadtmüller, C. E. Tucker, A. Vaupel, P. Knochel, Tetrahedron Lett. 1993, 34, 7911;
60. e) H. Stadtmüller, R. Lenz, C. E. Tucker, T. Stüdemann, W. Dörner, P. Knochel, J. Am. Chem. Soc. 1993, 115, 7027.