Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates

Synthesis

Volumn , Issue 21, 2006, Pages 3547-3574

  Korn, Tobias J ^a   Schade, Matthias A ^a   Cheemala, Murthy N ^a   Wirth, Stefan ^a   Guevara, Simon A ^a   Cahiez, Gérard ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cross coupling; Halides; Heterocycles; Magnesium; Transition metals

Indexed keywords

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CATALYSIS; MAGNESIUM PRINTING PLATES; TRANSITION METAL COMPOUNDS;

CROSS-COUPLING REACTIONS; HALIDES; HETEROCYCLES; POLYFUNCTIONALIZED AROMATICS;

CHLORINE COMPOUNDS;

BROMIDE; CHLORIDE; COBALT; COPPER; FLUORIDE; MAGNESIUM; TOLUENESULFONIC ACID DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33751318942     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950290     Document Type: Article

References (113)

1. (a) Metal Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
2. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002.
3. (c) Transition Metals for Organic Synthesis, 2nd ed.; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004.
4. Beller, M.; Zapf, A.; Mägerlein, W. Chem. Eng. Technol. 2001, 24, 575.
5. (a) Tan, Z.; Negishi, E. Synthesis of natural products via palladium-catalyzed cross-coupling, In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002, 863.
6. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442.
7. (a) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487.
8. (b) Tamura, M.; Kochi, J. K. Synthesis 1971, 93, 303.
9. (c) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351.
10. (d) Neumann, S.; Kochi, J. K. J. Org. Chem. 1975, 40, 599.
11. (e) Smith, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502.
12. (a) Cahiez, G.; Marquais, S. Pure Appl. Chem. 1996, 68, 669.
13. (b) Cahiez, G.; Marquais, S. Tetrahedron Lett. 1996, 37, 1773.
14. (c) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199.
15. (d) Cahiez, G.; Chaboche, C.; Mahuteau-Betzer, F.; Ahr, M. Org. Lett. 2005, 7, 1943.
16. (a) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
17. (b) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609.
18. (c) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2003, 42, 308.
19. (d) Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943.
20. (e) Martin, R.; Fürstner, A. Angew. Chem. Int. Ed. 2004, 43, 3955.
21. (f) Fürstner, A.; Martin, R.; Majima, K. J. Am. Chem. Soc. 2005, 127, 12236.
22. (a) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2001, 122, 978.
23. (b) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686.
24. (c) Nakamura, M.; Ito, S.; Matsuo, K.; Nakamura, E. Synlett 2005, 1794.
25. (a) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297.
26. (b) Nagano, T.; Hayashi, T. Org. Lett. 2005, 7, 491.
27. (a) Bedford, R. B.; Bruce, D. W.; Frost, R. M.; Goodby, J. W.; Hird, M. Chem. Commun. 2004, 2822.
28. (b) Bedford, R. B.; Bruce, D. W.; Frost, R. M.; Hird, M. Chem. Commun. 2005, 4161.
29. (a) For a review on iron-catalyzed reactions, see: Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
30. (b) Molander, G.; Rahn, B.; Shubert, D. C.; Bonde, S. E. Tetrahedron Lett. 1983, 24, 5449.
31. (c) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901.
32. (d) Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem. Int. Ed. 2001, 40, 621.
33. (e) Fakhfakh, M. A.; Franck, X.; Hocquemiller, R.; Figadère, B. J. Organomet. Chem. 2001, 624, 131.
34. (f) Hölzer, B.; Hoffmann, R. W. Chem. Commun. 2003, 732.
35. (g) Shinokubo, H.; Oshima, K. Eur. J. Org. Chem. 2004, 2081.
36. Sapountzis, I.; Lin, W.; Kofink, C. C.; Despotopoulou, C.; Knochel, P. Angew. Chem. Int. Ed. 2005, 44, 1654.
37. (a) Kharasch, M. S.; Fuchs, C. F. J. Am. Chem. Soc. 1943, 65, 504.
38. (b) Kharasch, M. S.; Fuchs, C. F. J. Org. Chem. 1945, 10, 292.
39. (c) Kharasch, M. S.; Urry, W. H. J. Org. Chem. 1948, 13, 101.
40. (a) Cahiez, G.; Avedissian, H. Tetrahedron Lett. 1998, 39, 6159.
41. (b) Avedissian, H.; Bérillon, L.; Cahiez, G.; Knochel, P. Tetrahedron Lett. 1998, 39, 6163.
42. (a) For a review, see: Shinokubo, H.; Oshima, K. Eur. J. Org. Chem. 2004, 2081.
43. (b) Fujioka, T.; Nakamura, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2002, 4, 2257.
44. (c) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem. Int. Ed. 2002, 41, 4137.
45. (d) Wakabayashi, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 5374.
46. (e) Ohmiya, H.; Tsuji, T.; Yorimitsu, H.; Oshima, K. Chem. Eur. J. 2004, 10, 5640.
47. (f) Ikeda, Y.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2002, 124, 6514.
48. (g) Mizutani, K.; Shinokubo, H.; Oshima, K. Org. Lett. 2003, 5, 3959.
49. (h) Ohmiya, H.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2004, 33, 1240.
50. (i) Ohmiya, H.; Yorimitsu, H.; Oshima, K. Angew. Chem. Int. Ed. 2005, 44, 2368.
51. (j) Ohmiya, H.; Yorimitsu, H.; Oshima, K. Angew. Chem. Int. Ed. 2005, 44, 3488.
52. (k) Ohmiya, H.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2006, 128, 1886.
53. (a) Gomes, P.; Gosmini, C.; Périchon, J. Org. Lett. 2003, 5, 1043.
54. (b) Gomes, P.; Gosmini, C.; Périchon, J. Synthesis 2003, 1909.
55. (c) Amatore, M.; Gosmini, C.; Périchon, J. Eur. J. Org. Chem. 2005, 989.
56. Korn, T. J.; Cahiez, G.; Knochel, P. Synlett 2003, 1892.
57. Korn, T. J.; Knochel, P. Angew. Chem. Int. Ed. 2005, 44, 2947.
58. Korn, T. J.; Schade, M. A.; Wirth, S.; Knochel, P. Org. Lett. 2006, 8, 725.
59. In the absence of the cobalt catalyst, full conversion (GC) was detected only after four days at room temperature.
60. For the preparation of functionalized arylmagnesium compounds, see: (a) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem. Int. Ed. 2003, 42, 4302.
61. (b) Knochel, P.; Krasovskiy, A.; Sapountzis, I. Polyfunctional Magnesium Organometallics for Organic Synthesis, In Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, 2005, 109.
62. Commercial cobalt powder was used (Aldrich, 99.9+% purity).
63. Commercial iron powder was used (Merck, ≥99.5% purity).
64. (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
65. (b) Taylor, R. J. K. Organocopper Reagents; Oxford University Press: Oxford, 1994.
66. (c) Krause, N. Modern Organocopper Chemistry; Wiley-VCH: Weinheim, 2002.
67. (a) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
68. (b) Besides CuCN·2LiCl, CuBr·2LiCl and CuSCN·2LiCl were also used for transmetalation, but CuCN·2LiCl gave better results
69. After 24 hours reaction time only 47% conversion was observed.
70. (a) Fiber, M.; Jensen, A. E.; Rottländer, M.; Knochel, P. Org. Lett. 1999, 1, 1323.
71. (b) Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
72. (c) Nguefack, J.-F.; Bollit, V.; Sinou, D. Tetrahedron Lett. 1996, 37, 5527.
73. (d) Powell, N. A.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 7901.
74. (e) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549.
75. (f) Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357.
76. Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67, 79.
77. 29% conversion was observed after four hours and 42% conversion after 21 hours reaction time at 80 °C.
78. Besides DMPU, NMP and N,N-dimethylacetamide (DMAC) also led to a rate acceleration, but DMPU showed the strongest effect.
79. For the preparation of benzofuranyllithium, see: Brown, H. C.; Gupta, A. K.; Prasad, J. V. N. V. Bull. Soc. Chem. Jpn. 1988, 61, 93.
80. For the preparation of ferrocenyllithium, see: Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502.
81. Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; Wiley-VCH: Weinheim, 1996.
82. Confirmed by HMBC-NMR analysis.
83. For a review on Pd-catalyzed cross-coupling reactions with aryl chlorides, see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
84. Selected examples: (a) Dankwardt, J. W. J. Organomet. Chem. 2005, 690, 932; and references cited therein.
85. (b) Bahmanyar, S.; Borer, B. C.; Kim, Y. M.; Kurtz, D. M.; Yu, S. Org. Lett. 2005, 7, 1011.
86. (c) Saeki, T.; Takashima, Y.; Tamao, K. Synlett 2005, 1771.
87. (d) Ackermann, L.; Born, R.; Spatz, J. H.; Meyer, D. Angew. Chem. Int. Ed. 2005, 44, 7216.
88. (a) Richmond, T. G. Angew. Chem. Int. Ed. 2000, 39, 3241.
89. (b) Braun, T.; Perutz, R. N. Chem. Commun. 2002, 2749.
90. No full conversion was observed if only 1.7 or 2 equivalents of copper reagent were used. In the absence of the cobalt-catalyst, no product was detected even after two days.
91. A mixture of mono- and two-fold cross-coupling product was obtained if only three equivalents of the arylcopper reagents 5l or 5i was used.
92. Selected examples: (a) Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
93. (b) Netherton, M. R.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 3910.
94. (c) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003,125, 6653.
95. (d) Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058; and references cited therein.
96. (e) Limmert, M. E.; Roy, A. H.; Hartwig, J. F. J. Org. Chem. 2005, 70, 9364; and references cited therein.
97. Wagner, P. J.; Sedon, J. H.; Gudmundsdottir, A. J. Am. Chem. Soc. 1996, 118, 746.
98. Ireland, T.; Tappe, K.; Grossheimann, G.; Knochel, P. Chem. Eur. J. 2002, 8, 843.
99. Moldenhauer, G.; Trautmann, G.; Irion, W.; Pfluger, R.; Döser, H.; Mastaglio, D.; Marwitz, H. Justus Liebigs Ann. Chem. 1953, 580, 169.
100. Susumu, K.; Takenori, N. R.; Hara, H.; Fujii, M.; Koutoku, H.; Oritani, H.; Mase, T. Chem. Pharm. Bull. 1999, 47, 1073.
101. Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748.
102. (a) Angu, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2004, 3, 353.
103. (b) Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 6, 801.
104. (c) Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M. G. O. Org. Lett. 2004, 16, 2741.
105. (d) Ackerman, L.; Born, R. Angew. Chem. Int. Ed. 2005, 16, 2444.
106. (e) Adjabeng, G.; Brenstrum, T.; Wilson, J.; Frampton, C.; Al, R.; Hillhouse, J.; McNulty, J.; Capretta, A. Org. Lett. 2003, 6, 953.
107. (f) Wang, L.; Zhang, Y.; Liu, L.; Wang, Y. J. Org. Chem. 2006, 3, 1284.
108. (g) Song, F.; Hilaire, V. R. S.; White, E. H. Org. Lett. 1999, 12, 1957.
109. (h) Nelly, L.; Alain, T.; Couture, K.; Queguiner, G. J. Org. Chem. 1995, 12, 3781.
110. (a) Gavryushin, A.; Kofink, C.; Manolikakes, G.; Knochel, P. Org. Lett. 2005, 22, 4871.
111. (b) Klement, I.; Rottlaender, M.; Tucker, C. E.; Majid, T. N.; Knochel, P.; Venegas, P.; Cahiez, G. Tetrahedron 1996, 21, 7201.
112. (c) Alam, N.; Amatore, C.; Combellas, C.; Pinson, J.; Saveant, M. J.; Thiebault, A.; Noel, V. J. J. Org. Chem. 1988, 53, 1496.
113. Sapountzis, I.; Lin, W.; Kofink, C.; Despotopoulou, C.; Knochel, P. Angew. Chem. Int. Ed. 2005, 11, 1654.