Ligand-free iron/copper cocatalyzed alkynylation coupling reactions

Advanced Synthesis and Catalysis

Volumn 350, Issue 16, 2008, Pages 2477-2482

  Mao, Jincheng ^a   Xie, Guanlei ^a   Wu, Minyan ^a   Guo, Jun ^a   Ji, Shunjun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Alkynylation coupling; Aryl halides; Cross coupling; Ligand free conditions; Terminal alkynes

Indexed keywords

EID: 56649108176     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800517     Document Type: Article

References (83)

1. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467-4470.
2. a) R. Chinchilla, C. Najera, Chem. Rev. 2007, 107, 874-922;
3. b) H. Doucet, J.-C. Hierso, Angew. Chem. 2007, 119, 850-880;
4. Angew. Chem. Int. Ed. 2007, 46, 834-871.
5. S. M. Thacher, S. Nagpal, E. S. Klein, T. Arefieg, G. Krasinski, D. DiSepio, C. Agarwal, A. Johnson, K. L. Eckert, R. A. S. Chandraratna, Cell Growth & Differentiation 1999, 10, 255-262.
6. a) M.W. Miller, C. R. Johnson, J. Org. Chem. 1997, 62, 1582-1583;
7. b) M. Xia, Y.-G. Wang, Chin. J. Org. Chem. 2003, 23, 609-612;
8. c) O. S. Miljanic, K. P. C. Vollhardt, G. D. Whitener, Synlett 2003, 29-34;
9. d) D. A. Shultz, K. P. Gwaleney, J. Org. Chem. 1998, 63, 4034-4038;
10. e) K. L. Yu, S. Chen, J. Ostrowski, Bioorg. Med. Chem. Lett. 1996, 6, 2859-2864;
11. f) L. Wang, P. H. Li, Chin. J. Chem. 2003, 21, 474-476.
12. a) S. Thorand, N. Krause, J. Org. Chem. 1998, 63, 8551-8553;
13. b) A. S. Karpov, F. Rominger, T. J. J. Muller, J. Org. Chem. 2003, 68, 1503-1511;
14. c) A. Elangovan, Y. H. Wang, Org. Lett. 2003, 5, 1841-1844;
15. d) J. F. Nguefack, V. Bollet, D. Sinou, Tetrahedron Lett. 1996, 37, 5527-5530;
16. e) Y. Koseki, K. Omino, S. Anzai, Tetrahedron Lett. 2000, 41, 2377-2380.
17. a) J.-H. Li, Q.-M. Zhu, Y.-X. Xie, J. Org. Chem. 2005, 70, 4393-4396;
18. b) J.-H. Li, D.-P. Wang, Y.-X. Xie, Eur. J. Org. Chem. 2005, 4256-4259;
19. c) T. Fukuyama, M. Shinmen, S. Nishitani, Org. Lett. 2002, 4, 1691-1694;
20. d) J.-H. Li, D.-P. Wang, Y.-X. Xie, J. Org. Chem. 2006, 71, 379-381;
21. e) L. Anastasia, E. Negishi, Org. Lett. 2001, 3, 3111-3113.
22. S. U. Son, Y. Jang, J. Park, H. B. Na, H. M. Park, H. J. Yun, J. Lee, T. Hyeon, J. Am. Chem. Soc. 2004, 126, 5026-5027.
23. R. Soler, . S. Cacchi, G. Fabrizi, G. Forte, L. Martín, S. Martínez, E. Molins, M. Moreno-Mañas, F. Petrucci, A. Roig, R. M. Sebastián, A. Vallribera, Synthesis 2007, 3068-3072.
24. Leading examples, see: a) M. Feuerstein, F. Berthiol, H. Doucet, M. Santelli, Org. Biomol. Chem. 2003, 1, 2235-2237;
25. b) J.-C. Hierso, A. Fihri, R. Amardell, P. Meunier, Org. Lett. 2004, 6, 3473-3476;
26. c) J.-C. Hierso, A. Fihri, R. Amardell, P. Meunier, H. Doucet, M. Santelli, Tetrahedron 2005, 61, 9759-9766;
27. d) J.-C. Hierso, M. Beaupéin, P. Meunier, Eur. J. Inorg. Chem. 2007, 3767-3780;
28. e) A. Köllhofer, H. Plenio, Adv. Synth. Catal. 2005, 347, 1295-1300.
29. I. P. Beletskaya, G. V. Latyshev, A. V. Tsvetkov, N. V. Lukashev, Tetrahedron Lett. 2003, 44, 5011-5013.
30. For special reviews on copper-catalyzed cross-couplings, see: a) P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740-2767;
31. Angew. Chem. Int. Ed. 2000, 39, 2632-2657;
32. b) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1470;
33. c) S. V. Ley, A.W. Thomas, Angew. Chem. 2003, 115, 5558-5607;
34. Angew. Chem. Int. Ed. 2003, 42, 5400-5449;
35. d) I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337-2364;
36. e) F. Monnier, F. Turtaut, L. Duroure, M. Taillefer, Org. Lett. 2008, 10, 3203-3206.
37. a) S. Cacchi, G. Fabrizi, L. M. Parisi, Org. Lett. 2003, 5, 3843-3846;
38. b) M. B. Thathagar, J. Beckers, G. Rothenberg, Green. Chem. 2004, 6, 215-218;
39. c) K. Okaro, M. Furuune, M. Enna, M. Miura, M. Nomura, J. Org. Chem. 1993, 58, 4716-4721;
40. d) B.-X. Tang, F. Wang, J.-H. Li, Y.-X. Xie, M.-B. Zhang, J. Org. Chem. 2007, 72, 6294-6297;
41. e) C. G. Bates, P. Saejueng, J. M. Murphy, D. Venkataraman, Org. Lett. 2002, 4, 4727-4729;
42. f) Y. F. Wang, W. Deng, L. Liu, Q. X. Guo, Chin. Chem. Lett. 2005, 16, 1197-1200;
43. g) J.-H. Li, J.-L. Li, D.-P. Wang, S.-F. Pi, Y.-X. Xie, M.-B. Zhang, X.-C. Hu, J. Org. Chem. 2007, 72, 2053-2057;
44. h) D. Ma, F. Liu, Chem. Commun. 2004, 1934-1935;
45. i) J. Mao, J. Guo, S.-J. Ji, J. Mol. Catal. A: Chem. 2008, 284, 85-88;
46. j) H. Plenio, Angew. Chem. 2008, 120, 7060-7063;
47. Angew. Chem. Int. Ed. 2008, 47, 6954-6956;
48. k) F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140-3143;
49. Angew. Chem. Int. Ed. 2008, 47, 3096-3099;
50. l) P. Saejueng, C. G. Bates, D. Venkataraman, Synthesis 2005, 1706-1712;
51. m) F. Liu, D. Ma, J. Org. Chem. 2007, 72, 4844-4850.
52. L. Wang, P. Li, Y. Zhang, Chem. Commun. 2004, 514-515.
53. A. Corma, C. González-Arellano, M. Iglesias, F. Sánchez, Angew. Chem. 2007, 119, 1558-1560;
54. Angew. Chem. Int. Ed. 2007, 46, 7820-7822.
55. S. Park, M. Kim, D. H. Koo, S. Chang, Adv. Synth. Catal. 2004, 346, 1638-1640.
56. For general reviews, see: a) C. Bolm, J. Legros, J. L. Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254;
57. b) A. Fürstner, R. Martin, Chem. Lett. 2005, 34, 624-629.
58. M. Taillefer, N. Xia, A. Oualli, Angew. Chem. 2007, 119, 952-954;
59. Angew. Chem. Int. Ed. 2007, 46, 934-936.
60. V. H. Jadhav, D. K. Dumbre, V. B. Phapale, H. B. Borate, R. D. Wakharkar, Catal. Commun. 2007, 8, 65-68.
61. a) A. Correa, C. Bolm, Angew. Chem. 2007, 119, 9028-9031;
62. Angew. Chem. Int. Ed. 2007, 46, 8862-8865;
63. b) A. Correa, C. Bolm, Adv. Synth. Catal. 2008, 350, 391-394;
64. c) A. Correa, S. Elmore, C. Bolm, Chem. Eur. J. 2008, 14, 3527-3529.
65. C-O coupling, see: a) O. Bistri, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 596-598;
66. Angew. Chem. Int. Ed. 2008, 47, 586-588;
67. b) N. Xia, M. Taillefer, Chem. Eur. J. 2008, 14, 6037-6039;
68. C-S coupling, see: c) A. Correa, M. Carril, C. Bolm, Angew. Chem. 2008, 120, 2922-2925;
69. Angew. Chem. Int. Ed. 2008, 47, 2880-2883.
70. a) Z. Wang, Y. Zhang, H. Fu, Y. Jiang, Y. Zhao, Org. Lett. 2008, 10, 1863-1866;
71. b) R. Li, S. R. Wang, W. Lu, Org. Lett. 2007, 9, 2219-2222;
72. c) J. Bonnamour, C. Bolm, Org. Lett. 2008, 10, 2665-2667.
73. 3-catalyzed Sonogashira coupling reaction using dmeda as the ligand. Please see: M. Carril, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 4940-4943;
74. Angew. Chem. Int. Ed. 2008, 47, 4862-4865.
75. a) J. Mao, J. Guo, S.-J. Ji, Tetrahedron 2008, 64, 1383-1387;
76. b) J. Mao, J. Guo, F. Fang, S.-J. Ji, Tetrahedron 2008, 64, 3905-3911;
77. c) Z. Xu, J. Mao, Y. Zhang, Catal. Commun. 2008, 9, 97-100.
78. D. Evrard, D. Lucas, Y. Mugnier, P. Meunier, J.-C. Hierso, Organometallics 2008, 27, 2643-2653.
79. A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 4844-4845.
80. a) R. R. Gupta, M. Kumar, V. Gupta, Heterocyclic Chemistry II. Springer Verlag, Berlin, Heidelberg, 1998, Vol. 2;
81. b) R. J. Sundberg, Indoles, Academic Press, San Diego, 1996.
82. a) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920;
83. b) G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911.