Cobalt(II)-catalyzed cross-coupling of polyfunctional aryl copper reagents with aryl bromides and chlorides

Angewandte Chemie - International Edition

Volumn 44, Issue 19, 2005, Pages 2947-2951

  Korn, Tobias J ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cobalt; Cross coupling; Grignard reagents; Heterocycles; Organocopper compounds

Indexed keywords

CROSS-COUPLING REACTIONS; HETEROAROMATIC COMPOUNDS; POLYFUNCTIONAL ARYL COPPER REAGENTS; TRANSMETALATION;

BROMINE COMPOUNDS; CATALYSIS; CHLORINE COMPOUNDS; COBALT; COPPER COMPOUNDS; ORGANOMETALLICS; STYRENE;

AROMATIC COMPOUNDS;

BENZOIC ACID DERIVATIVE; BROMINE; CHLORINE; COBALT; COPPER; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

BENZOATES; BROMINE; CATALYSIS; CHLORINE; COBALT; COPPER; MOLECULAR STRUCTURE; ORGANIC CHEMICALS;

EID: 18844429513     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500099     Document Type: Article

References (93)

1. a) Metal-catalyzed Cross-coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd. ed., Wiley-VCH, Weinheim, 2004;
2. b) J. Tsuji, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995;
3. c) "Cross-Coupling Reactions: A Practical Guide": Top. Curr. Chem. 2002, 219;
4. d) Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley-Interscience, New York, 2002;
5. e) Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998.
6. a) C. Dai, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 2719;
7. b) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989;
8. c) A. F. Littke, L. Schwarz, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 6343;
9. d) A. F. Littke, G C. Fu, Angew. Chem. 2002, 114, 4350;
10. Angew. Chem. Int. Ed. 2002, 41, 4176;
11. e) I. D. Hills, M. R. Netherton, G. C. Fu, Angew. Chem. 2003, 115, 5927;
12. Angew. Chem. Int. Ed. 2003, 42, 5749;
13. f) A. C. Frisch, A. Zapf, O. Briel, B. Kayser, N. Shaikh, M. Beller, J. Mol. Catal. A 2004, 214, 231;
14. g) A. Tewari, M. Hein, A. Zapf, M. Beller, Synthesis 2004, 935;
15. h) F. Rataboul, A. Zapf, R. Jackstell, S. Harkal, T. Riermeier, A. Monsees, U. Dingerdissen, M. Beller, Chem. Eur. J. 2004, 10, 2983;
16. i) M. Kumada, Pure Appl. Chem. 1980, 52, 669;
17. j) T.-Y. Luh, Acc. Chem. Res. 1991, 24, 257;
18. k) S. Sengupta, M. Leite, D. S. Raslan, C. Quesnelle, V. Snieckus, J. Org. Chem. 1992, 57, 4066;
19. l) A. F. Indolese, Tetrahedron Lett. 1997, 38, 3513;
20. m) E. Shirakawa, K. Yamasaki, T. Hiyama, Synthesis 1998, 1544;
21. n) A. Sophia, E. Karlström, K. Itami, J.-E. Bäckvall, J. Am. Chem. Soc. 2000, 122, 6950;
22. o) J. Montgomery, Acc. Chem. Res. 2000, 33, 467;
23. p) R. Giovaninni, P. Knochel, J. Am. Chem. Soc. 1998, 120, 11186;
24. q) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313;
25. r) B. H. Lipshutz, G. Bulwo, F. Fernandez-Lazaro, S.-K. Kim, R. Lowe, P. Mollard, K. L. Stevens, J. Am. Chem. Soc. 1999, 121, 11 664.
26. a) M. Tamura, J. K. Kochi, J. Am. Chem. Soc. 1971, 93, 1487;
27. b) M. Tamura, J. K. Kochi, Synthesis 1971, 93, 303;
28. c) M. Tamura, J. K. Kochi, J. Organomet. Chem. 1971, 31, 289;
29. d) M. Tamura, J. K. Kochi, Bull. Chem. Soc. Jpn. 1971, 44, 3063;
30. e) M. Tamura, J. K. Kochi, Synthesis 1971, 303;
31. f) J. K. Kochi, Acc. Chem. Res. 1974, 7, 351;
32. g) S. Neumann, J. K. Kochi, J. Org. Chem. 1975, 40, 599;
33. h) R. S. Smith, J. K. Kochi, J. Org. Chem. 1976, 41, 502;
34. i) see also: G. Molander, B. Rahn, D. C. Shubert, S. E. Bonde, Tetrahedron Lett. 1983, 24, 5449;
35. j) G. Cahiez, S. Marquais, Pure Appl. Chem. 1996, 68, 669;
36. k) G. Cahiez, S. Marquais, Tetrahedron Lett. 1996, 37, 1773;
37. l) G. Cahiez, H. Avedissian, Synthesis 1998, 1199;
38. m) H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2081;
39. n) M. A. Fakhfakh, X. Franck, R. Hocquemiller, B. Figadère, J. Organomet. Chem. 2001, 624, 131;
40. o) M. Hocek, H. Dvoráková, J. Org. Chem. 2003, 68, 5773;
41. p) B. Hölzer, R. W. Hoffmann, Chem. Commun. 2003, 732;
42. q) W. Dohle, F. Kopp, G. Cahiez, P Knochel, Synlett 2001, 1901;
43. r) M. Hojo, Y. Murakami, H. Aihara, R. Sakuragi, Y. Baba, A. Hosomi, Angew. Chem. 2001, 113, 641;
44. Angew. Chem. Int. Ed. 2001, 40, 621;
45. s) M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2001, 123, 978;
46. t) E. Alvarez, T. Cuvigny, C. H. du Penhoat, M. Julia, Tetrahedron 1998, 54, 119;
47. u) V. Finandanese, G. Marchese, V. Martina, L. Ronzini, Tetrahedron Lett. 1984, 25, 4805.
48. I. Sapountzis, W. Lin, C. C. Kofink, C. Despotopoulou, P. Knochel, Angew. Chem. 2005, 117, 1682;
49. Angew. Chem. Int. Ed. 2005, 44, 1654.
50. a) For an excellent review on iron-catalyzed reactions, see: C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217;
51. b) A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13 856;
52. c) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632;
53. Angew. Chem. Int. Ed. 2002, 41, 609;
54. d) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320;
55. Angew. Chem. Int. Ed. 2003, 42, 308;
56. e) G. Seidel, D. Laurich, A. Fürstner, J. Org. Chem. 2004, 69, 3950;
57. f) B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943;
58. g) A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516;
59. Angew. Chem. Int. Ed. 2003, 42, 5355;
60. h) M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686;
61. i) T. Nagano, T. Hayashi, Org. Lett. 2004, 6, 1297;
62. j) R. Martin, A. Fürstner, Angew. Chem. 2004, 116, 4045;
63. Angew. Chem. Int. Ed. 2004, 43, 3955;
64. k) R. B. Bedford, D. W. Bruce, R. M. Frost, J. W. Goodby, M. Hird, Chem. Commun. 2004, 2822.
65. C. K. Reddy, P. Knochel, Angew. Chem. 1996, 108, 1812;
66. Angew. Chem. Int. Ed. Engl. 1996, 35, 1700.
67. T. J. Korn, G. Cahiez, P. Knochel, Synlett 2003, 1892.
68. a) H. Avedissian, L. Bérillon, G. Cahiez, P. Knochel, Tetrahedron Lett. 1998, 39, 6163;
69. b) G. Cahiez, H. Avedissian, Tetrahedron Lett. 1998, 39, 6159.
70. a) For an excellent review, see: H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2081;
71. b) T. Fujioka, T. Nakamura, H. Yorimitsu, K. Oshima, Org. Lett. 2002, 4, 2257;
72. c) T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. 2002, 114, 4311;
73. Angew. Chem. Int. Ed. 2002, 41, 4137;
74. d) K. Wakabayashi, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2001, 123, 5374;
75. e) H. Ohmiya, T. Tsuji, H. Yorimitsu, K. Oshima, Chem. Eur. J. 2004, 10, 5640;
76. f) Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2002, 124, 6514;
77. g) K. Mizutani, H. Shinokubo, K. Oshima, Org. Lett. 2003, 5, 3959.
78. a) P. Gomes, C. Gosmini, J. Périchon, Org. Lett. 2003, 5, 1043;
79. b) P. Gomes, C. Gosmini, J. Périchon, Synthesis 2003, 1909.
80. a) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135;
81. b) R. J. K. Taylor, Organocopper Reagents, Oxford University Press, Oxford, 1994;
82. c) N. Krause, Modern Organocopper Chemistry, Wiley-VCH, Weinheim, 2002.
83. P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 55, 2390.
84. After a reaction time of 24 h only 47% conversion was observed.
85. a) M. Piber, A. E. Jensen, M. Rottländer, P. Knochel, Org. Lett. 1999, 1, 1323;
86. b) S. W. Wright, D. L. Hageman, L. D. McClure, J. Org. Chem. 1994, 59, 6095;
87. c) J.-F. Nguefack, V. Bollit, D. Sinou, Tetrahedron Lett. 1996, 37, 5527;
88. d) N. A. Powell, S. D. Rychnovsky, Tetrahedron Lett. 1996, 37, 7901;
89. e) K. Nakamura, H. Okubo, M. Yamaguchi, Synlett 1999, 549;
90. f) W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357.
91. A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79.
92. After a reaction time of 4 h at 80°C, 29% conversion was observed, and after 21 h, 42% conversion was observed.
93. Besides DMPU, 1-methyl-2-pyrrolidinone (NMP) and N,N-dimethylacetamide (DMAC) also led to a rate acceleration when used as cosolvents, but DMPU showed the strongest effect.