Copper-catalyzed decarboxylase cross-coupling of potassium polyfluorobenzoates with aryl iodides and bromides

Angewandte Chemie - International Edition

Volumn 48, Issue 49, 2009, Pages 9350-9354

  Shang, Rui ^a,b   Fu, Yao ^a,b   Wang, Yan ^a,b   Xu, Qing ^a,b   Yu, Hai Zhu ^a,b   Liu, Lei ^a,b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

Copper; Cross coupling; Homogeneous catalysis; Polyfluoroarenes; Reaction mechanisms

Indexed keywords

ARYL IODIDES; COPPER CATALYST; CROSS-COUPLINGS; DECARBOXYLASES; HOMOGENEOUS CATALYSIS; MECHANISTIC ANALYSIS; NON-VOLATILE; POLYFLUOROARENES; REACTION MECHANISM;

BROMINE COMPOUNDS; CATALYSIS; CATALYSTS; POTASSIUM; REACTION KINETICS;

COPPER;

EID: 72949087126     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904916     Document Type: Article

References (89)

1. a) O. Baudoin, Angew. Chem. 2007, 119, 1395;
2. Angew. Chem. Int. Ed. 2007, 46, 1373;
3. b) L. J. Goossen, N. Rodriguez, K. Goossen, Angew. Chem. 2008, 120, 3144;
4. Angew. Chem. Int. Ed. 2008, 47, 3100.
5. a) M. Nilsson, Acta Chem. Scand. 1966, 20, 423;
6. b) C. Björklund, M. Nilsson, Acta Chem. Scand. 1968, 22, 2585;
7. c) A. Cairncross, J. R. Roland, R. M. Henderson, W. A. Shepard, J. Am. Chem. Soc. 1970, 92, 3187;
8. d) T. Cohen, R. A. Schambach, J. Am. Chem. Soc. 1970, 92, 3189.
9. a) L. J. Goossen, G. Deng, L. M. Levy, Science 2006, 313, 662;
10. b) L. J. Goossen, N. Rodriguez, B. Melzer, C. Linder, G. Deng, L. M. Levy, J. Am. Chem. Soc. 2007, 129, 4824;
11. c) L. J. Goossen, B. Melzer, J. Org. Chem. 2007, 72, 7473;
12. d) L. J. Goossen, T. Knauber, J. Org. Chem. 2008, 73, 8631;
13. e) L. J. Goossen, B. Zimmermann, T. Knauber, Angew. Chem. 2008, 120, 7211;
14. Angew. Chem. Int. Ed. 2008, 47, 7103;
15. f) L.J. Goossen, N. Rodriguez, C. Linder, J. Am. Chem. Soc. 2008, 130, 15248;
16. g) L. J. Goossen, F. Rudolphi, C. Oppel, N. Rodriguez, Angew. Chem. 2008, 120, 3085;
17. Angew. Chem. Int. Ed. 2008, 47, 3043.
18. a) A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250;
19. b) D. Tanaka, A. G. Myers, Org. Lett. 2004, 6, 433;
20. c) D. Tanaka, S. P. Romeril, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 10323.
21. P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350.
22. a) J. Moon, M. Jeong, H. Nam, J. Ju, J. H. Moon, H. M. Jung, S. Lee, Org. Lett. 2008, 10, 945;
23. b) J. Moon, M. Jang, S. Lee, J. Org. Chem. 2009, 74, 1403.
24. a) J.-M. Becht, C. Le Drian, Org. Lett 2008, 10, 3161;
25. b) J.-M. Becht, C. Catala, C. Le Drian, A. Wagner, Org. Lett. 2007, 9, 1781.
26. a) Z. Y. Wang, Q. P. Ding, X. D. He, J. Wu, Org. Biomol. Chem. 2009, 7, 863;
27. b) Z. Y. Wang, Q. P. Ding, X. D. He, J. Wu, Tetrahedron 2009, 65, 4635;
28. c) A. Voutchkova, A. Coplin, N. E. Leadbeater, R. H. Crabtree, Chem. Commun. 2008, 6312.
29. C. Wang, I. Piel, F. Glorius, J. Am. Chem. Soc. 2009, 131, 4194.
30. R. Shang, Y. Fu, J. B. Li, S. L. Zhang, Q. X. Guo, L. Liu, J. Am. Chem. Soc. 2009, 131, 5738.
31. a) S. R. Waetzig, D. K. Rayabarupu, J. D. Weaver, J. A. Tunge, Angew. Chem. 2006, 118, 5099;
32. Angew. Chem. Int. Ed. 2006,45, 4977;
33. b) S. R. Waetzig, J. A. Tunge, J. Am. Chem. Soc. 2007, 129, 14860;
34. c) W. H. Fields, A. K. Khan, M. Sabat, J. J. Chruma, Org. Lett. 2008, 10, 5131;
35. d) S.-F. Pi, B.-X. Tang, J.-H. Li, Y.-L. Liu, Y. Liang, Org. Lett. 2009, 11, 2309;
36. e) H.-P. Bi, L. Zhao, Y.-M. Liang, C.-J. Li, Angew. Chem. 2009, 121, 806;
37. Angew. Chem. Int. Ed. 2009, 48,792;
38. f) H.-P. Bi, W.-W. Chen, Y.-M. Liang, C.-J. Li, Org. Lett. 2009, 11, 3246;
39. g) Z. Duan, S. Ranjit, P. Zhang, X. Liu, Chem. Eur. J. 2009, 15, 3666;
40. h) A. A. Yeagley, M. A. Lowder, J. J. Chruma, Org. Lett. 2009, 11, 4022;
41. i) P. Hu, J. Kan, W. Su, M. Hong, Org. Lett. 2009, 11, 2341;
42. j) W.-Y. Yu, W. Sit, Z. Zhou, A. S.-C. Chan, Org. Lett 2009, 11, 3174;
43. k) M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, M. Miura, Chem. Eur. J. 2009, 75, 3674.
44. There are two literature examples for palladium-catalyzed decarboxylative coupling of perfluorobenzoic acid with 4iodoanisole; see references [7b, 8c].
45. For a special protocol for the Suzuki-Miyaura coupling reaction of pentafluorophenylboronic acid, which is an inactive substrate under normal conditions, see: T. Korenaga, T. Kosaki, R. Fukumura, T. Ema, T. Sakai, Org. Lett. 2005, 7, 4915.
46. a) R. E. Mewshaw, R. J. Edsall, Jr., C. Yang, E. S. Manas, Z. B. Xu, R. A. Henderson, J. C. Keith, Jr., H. A. Harris, J. Med. Chem. 2005, 48, 3953;
47. b) M. de Candia, F. Liantonio, A. Carotti, R. De Cristofaro, C. Altomare, J. Med. Chem. 2009, 52, 1018.
48. a) J. R. Nitschke, T. D. Tilley, J. Am. Chem. Soc. 2001, 123, 10183;
49. b) P. Zacharias, M. C. Gather, M. Rojahn, O. Nuyken, K. Meerholz, Angew. Chem 2007, 119, 4467;
50. Angew. Chem. Int. Ed. 2007, 46, 4388.
51. a) M. Lafrance, C. N. Rowley, T. K. Woo, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 8754;
52. b) M. Lafrance, D. Shore, K. Fagnou, Org. Lett. 2006, 8, 5097.
53. a) H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129,12404;
54. b)H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2008, 130, 1128;
55. c) H.-Q. Do, R. M. Kashif Khan, O. Daugulis, J. Am. Chem. Soc. 2008, 130, 15185.
56. L. J. Goossen, F. Manjolinho, B. A. Khan, N. Rodriguez, J. Org. Chem. 2009, 74, 2620.
57. Reviews for copper-catalyzed cross-couplings: a) S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558;
58. Angew. Chem. Int. Ed. 2003, 42, 5400;
59. b) W. Deng, L. Liu, Q.-X. Guo, Chin. J. Org. Chem. 2004, 24, 150;
60. c) D. Ma, Q. Cai, Acc. Chem. Res. 2008, 41,1450;
61. d) F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140;
62. Angew. Chem. Int. Ed. 2008, 47, 3096;
63. e) G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054.
64. For selected examples of copper-catalyzed cross-couplings, see: a) A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727;
65. b) R. A. Altman, A. M. Hyde, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 9613;
66. c) D. Ma, Y. Zhang, J. Yao, S. Wu, F. Tao, J. Am. Chem. Soc. 1998, 120, 12459;
67. d) D. Ma, S. Xie, P. Xue, X. Zhang, J. Dong, Y. Jiang, Angew. Chem. Int. Ed. 2009, 48, 4222;
68. e) M. B. Thathagar, J. Beckers, G. Rothenberg, J. Am. Chem. Soc. 2002, 124, 11858;
69. f) V. del Amo, S. R. Dubbaka, A. Krasovskiy, P. Knochel, Angew. Chem. 2006, 118, 8002;
70. Angew. Chem. Int. Ed. 2006, 45, 7838;
71. g) X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790;
72. h) J. M. Villalobos, J. Srogl, L. S. Libeskind, J. Am. Chem. Soc. 2007, 129, 15734;
73. i) H. Prokopcova, C. O. Kappe, Angew. Chem. 2008, 120, 3732;
74. Angew. Chem. Int. Ed. 2008, 47, 3674;
75. j) P. H. Fuller, J.-W. Kim, S. R. Chemler, J. Am. Chem. Soc. 2008, 130, 17638;
76. k) A. E. King, T. C. Brunold, S. S. Stahl, J. Am. Chem. Soc. 2009, 131, 5044;
77. l) R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593.
78. L. J. Goossen, W. R. Thiel, N. Rodriguez, C. Linder, B. Melzer, Adv. Synth. Catal. 2007, 349, 2241.
79. Some previous studies on the mechanism of copper-catalyzed cross-couplings: a) A. Ouali, J.-F. Spindler, A. Jutand, M. Taillefer, Adv. Synth. Catal. 2007, 349, 1906;
80. b) S.-L. Zhang, L. Liu, Y. Fu, Q.-X. Guo, Organometallics 2007, 26, 4546;
81. c) A. Ouali, M. Taillefer, J.-F. Spindler, A. Jutand, Organometallics 2007, 26, 65;
82. d) J. W. Tye, Z. Weng, A. M. Johns, C. D. Incarvito, J.F. Hartwig, J. Am. Chem. Soc. 2008, 130, 9971;
83. e) L. M. Huffman, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 9196;
84. f) H. Kaddouri, V. Vicente, A. Ouali, F. Ouazzani, M. Taillefer, Angew. Chem. 2009, 121, 339;
85. Angew. Chem. Int. Ed. 2009, 48, 333;
86. g) E. R. Strieter, B. Bhayana, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 78.
87. Earlier studies already showed that pentafluorophenylcopper can react with aryl iodides producing coupling products in high yield. See : a) A. Cairncross, W. A. Sheppard, J. Am. Chem. Soc. 1968, 90, 2186;
88. b) W. A. Sheppard, J. Am. Chem. Soc. 1970, 92, 5419.
89. Thermal ellipsoids shown at 50% probability. CCDC-752845 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif.