Gold-catalyzed cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile synthesis of diversified carbazoles

Chemistry - A European Journal

Volumn 19, Issue 32, 2013, Pages 10625-10631

  Zhang, Zhen ^a   Tang, Xiangying ^a   Xu, Qin ^b   Shi, Min ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

carbazoles; catalysis; cyclization; gold; indoles

Indexed keywords

CARBAZOLES; CYCLOPROPYL GROUP; INDOLES; METAL-CARBENE INTERMEDIATES; NUCLEOPHILIC ATTACK; REACTION CONDITIONS; REACTION PATHWAYS; SUBSTITUTION PATTERNS;

CATALYSIS; ELECTROPOLYMERIZATION; GOLD; POLYCYCLIC AROMATIC HYDROCARBONS;

CYCLIZATION;

ALKYNE; CARBAZOLE; CARBAZOLE DERIVATIVE; GOLD; INDOLE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CARBAZOLES; CATALYSIS; CYCLIZATION; GOLD; INDOLES;

ALKYNES; CARBAZOLES; CATALYSIS; CYCLIZATION; GOLD; INDOLES; SOLVENTS;

EID: 84880951851     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301203     Document Type: Article

References (100)

1. H.-J. Knölker, Top. Curr. Chem. 2005, 244, 115-148
2. C. Sánchez, C. Mèndez, J. A. Salas, Nat. Prod. Rep. 2006, 23, 1007-1045
3. M. Prudhomme, Eur. J. Med. Chem. 2003, 38, 123-140
4. C. Ito, M. Itoigawa, A. Sato, C. M. Hasan, M. A. Rashid, H. Tokuda, T. Mukainaka, H. Nishino, H. Furukawa, J. Nat. Prod. 2004, 67, 1488-1491
5. W. Maneerat, T. Ritthiwigrom, S. Cheenpracha, T. Promgool, K. Yossathera, S. Deachathai, W. Phakhodee, S. Laphookhieo, J. Nat. Prod. 2012, 75, 741-746
6. K. Takada, H. Kajiwara, N. Imamura, J. Nat. Prod. 2010, 73, 698-701
7. S. Oishi, T. Watanabe, J. Sawada, A. Asai, H. Ohno, N. Fujii, J. Med. Chem. 2010, 53, 5054-5058.
8. A. Van Dijken, J. J. A. M. Bastiaansen, N. M. M. Kiggen, B. M. W. Langeveld, C. Rothe, A. Monkman, I. Bach, P. Sössel, K. Brunner, J. Am. Chem. Soc. 2004, 126, 7718-7727
9. N. Blouin, A. Michaud, D. Gendron, S. Wakim, E. Blair, R. Neagu-Plesu, M. Belletête, G. Durocher, Y. Tao, M. Leclerc, J. Am. Chem. Soc. 2008, 130, 732-742
10. S. Wakim, J. Bouchard, M. Simard, N. Drolet, Y. Tao, M. Leclerc, Chem. Mater. 2004, 16, 4386-4388
11. K. R. J. Thomas, J. T. Lin, Y.-T. Tao, C.-W. Ko, J. Am. Chem. Soc. 2001, 123, 9404-9411.
12. G. A. Sotzing, J. L. Reddinger, A. R. Katritzky, J. Soloducho, R. Musgrave, J. R. Reynolds, Chem. Mater. 1997, 9, 1578-1587
13. J. Doskocz, M. Doskocz, S. Roszak, J. Soloducho, J. Leszczynski, J. Phys. Chem. A 2006, 110, 13989-13994
14. G. Zotti, G. Schiavon, S. Zecchin, J.-F. Morin, M. Leclerc, Macromolecules 2002, 35, 2122-2128.
15. M. R. TePaske, J. B. Gloer, J. Org. Chem. 1989, 54, 4743-4746
16. J. B. Gloer, B. L. Rinderknecht, D. T. Wicklow, P. F. Dowd, J. Org. Chem. 1989, 54, 2530-2532.
17. L. Ding, J. Münch, H. Goerls, A. Maier, H.-H. Fiebig, W.-H. Lin, C. Hertweck, Bioorg. Med. Chem. Lett. 2010, 20, 6685-6687
18. H. Li, Q. Zhang, S. Li, Y. Zhu, G. Zhang, H. Zhang, X. Tian, S. Zhang, J. Ju, C. Zhang, J. Am. Chem. Soc. 2012, 134, 8996-9005
19. L. Ding, A. Maier, H. H. Fiebig, W. H. Lin, C. Hertweck, Org. Biomol. Chem. 2011, 9, 4029-4031.
20. G. Lin, A. Zhang, Tetrahedron 2000, 56, 7163-7171
21. A. Zhang, G. Lin, Bioorg. Med. Chem. Lett. 2000, 10, 1021-1023.
22. J. Roy, A. K. Jana, D. Mal, Tetrahedron 2012, 68, 6099-6121
23. H.-J. Knölke, Chem. Lett. 2009, 38, 8-13
24. H.-J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303-4428
25. C. J. Moody, Synlett 1994, 681-688
26. J. Bergman, B. Pelcman, Pure Appl. Chem. 1990, 62, 1967-1976
27. M. Toyota, M. Ihara, Nat. Prod. Rep. 1998, 15, 327-340.
28. M. F. Martínez-Esperõn, D. Rodríguez, L. Castedo, C. Saá, Org. Lett. 2005, 7, 2213-2216
29. T. Tsuchimoto, H. Matsubayashi, M. Kaneko, E. Shirakawa, Y. Kawakami, Angew. Chem. 2005, 117, 1360-1364
30. Angew. Chem. Int. Ed. 2005, 44, 1336-1340
31. M. F. Martínez-Esperõn, D. Rodríguez, L. Castedo, C. Saá, Tetrahedron 2008, 64, 3674-3686
32. A. K. Mohanakrishnan, V. Dhayalan, J. A. Clement, R. B. R. Sureshbabu, N. S. Kumar, Tetrahedron Lett. 2008, 49, 5850-5854
33. U. K. S. Kumar, P. K. Patra, H. Ila, H. Junjappa, Tetrahedron Lett. 1998, 39, 2029-2032
34. C. Wang, W. Zhang, S. Lu, J. Wu, Z. Shi, Chem. Commun. 2008, 5176-5178.
35. C. Ferrer, A. M. Echavarren, Angew. Chem. 2006, 118, 1123-1127
36. Angew. Chem. Int. Ed. 2006, 45, 1105-1109
37. C. Liu, R. A. Widenhoefer, Org. Lett. 2007, 9, 1935-1938
38. J. Barluenga, M. Piedrafita, A. Ballesteros, Á. L. Suárez-Sobrino, J. M. González, Chem. Eur. J. 2010, 16, 11827-11831
39. R. M. Zeldin, F. D. Toste, Chem. Sci. 2011, 2, 1706-1709
40. X. Xie, X. Du, Y. Chen, Y. Liu, J. Org. Chem. 2011, 76, 9175-9181
41. G. Cera, P. Crispino, M. Monari, M. Bandini, Chem. Commun. 2011, 47, 7803-7805
42. M. Bandini, Chem. Soc. Rev. 2011, 40, 1358-1367
43. A. S. K. Hashmi, W. Yang, F. Rominger, Adv. Synth. Catal. 2012, 354, 1273-1279
44. L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804-16805.
45. L. Wang, G. Li, Y. Liu, Org. Lett. 2011, 13, 3786-3789
46. Y. Qiu, W. Kong, C. Fu, S. Ma, Org. Lett. 2012, 14, 6198-6201
47. B. Alcaide, P. Almendros, J. M. Alonso, M. T. Quirõs, P. Gadzińskia, Adv. Synth. Catal. 2011, 353, 1871-1876
48. W. Kong, C. Fu, S. Ma, Chem. Commun. 2009, 4572-4574
49. W. Kong, C. Fu, S. Ma, Chem. Eur. J. 2011, 17, 13134-13137
50. W. Kong, C. Fu, S. Ma, Org. Biomol. Chem. 2012, 10, 2164-2173
51. W. Kong, Y. Qiu, C. Fu, S. Ma, Adv. Synth. Catal. 2012, 354, 2339.
52. K. Hirano, Y. Inaba, T. Watanabe, S. Oishi, N. Fujii, H. Ohno, Adv. Synth. Catal. 2010, 352, 368-372
53. K. Hirano, Y. Inaba, N. Takahashi, M. Shimano, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem. 2011, 76, 1212-1227
54. B. Witulski, C. Alayrac, Angew. Chem. 2002, 114, 3415-3418
55. Angew. Chem. Int. Ed. 2002, 41, 3281-3284.
56. For the synthesis of 1-(indol-3-yl)-3-alkyn-1-ol, see:, M. Miao, J. Cao, J. Zhang, X. Huang, L. Wu, Org. Lett. 2012, 14, 2718-2721.
57. P. Pérez-Galán, N. Delpont, E. Herrero-Gõmez, F. Maseras, A. M. Echavarren, Chem. Eur. J. 2010, 16, 5324-5332
58. E. Herrero-Gõmez, C. Nieto-Oberhuber, S. Lõpez, J. Benet-Buchholz, A. M. Echavarren, Angew. Chem. 2006, 118, 5581-5585
59. Angew. Chem. Int. Ed. 2006, 45, 5455-5459
60. C. R. Solorio-Alvarado, A. M. Echavarren, J. Am. Chem. Soc. 2010, 132, 11881-11883
61. C. R. Solorio-Alvarado, Y. Wang, A. M. Echavarren, J. Am. Chem. Soc. 2011, 133, 11952-11955
62. C. Nieto-Oberhuber, S. Lõpez, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179
63. V. Lõpez-Carrillo, A. M. Echavarren, J. Am. Chem. Soc. 2010, 132, 9292-9294.
64. G. Li, Y. Liu, J. Org. Chem. 2010, 75, 3526-3528.
65. J. Zhang, H.-G. Schmalz, Angew. Chem. 2006, 118, 6856-6859
66. Angew. Chem. Int. Ed. 2006, 45, 6704-6707
67. S. Labsch, S. Ye, A. Adler, J.-M. Neudörfl, H.-G. Schmalz, Tetrahedron: Asymmetry 2010, 21, 1745-1751.
68. A. S. K. Hashmi, Angew. Chem. 2010, 122, 5360-5369
69. Angew. Chem. Int. Ed. 2010, 49, 5232-5241.
70. Z. G. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265
71. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378
72. M. Rudolph, A. S. K. Hashmi, Chem. Commun. 2011, 47, 6536-6544
73. M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448-2462.
74. G. Cera, M. Chiarucci, A. Mazzanti, M. Mancinelli, M. Bandini, Org. Lett. 2012, 14, 1350-1353
75. S. G. Modha, A. Kumar, D. D. Vachhani, J. Jacobs, S. K. Sharma, V. S. Parmar, L. Van Meervelt, E. V. Van der Eycken, Angew. Chem. 2012, 124, 9710-9713
76. Angew. Chem. Int. Ed. 2012, 51, 9710-9713; for gold carbenes, see
77. A. S. K. Hashmi, Angew. Chem. 2008, 120, 6856-6858
78. Angew. Chem. Int. Ed. 2008, 47, 6754-6756
79. M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10858-10859
80. C. Nieto-Oberhuber, P. Pérez-Galán, E. Herrero-Gõmez, T. Lauterbach, C. Rodríguez, S. Lõpez, C. Bour, A. Rosellõn, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2008, 130, 269-279
81. R. Sanz, D. Miguel, F. Rodríguez, Angew. Chem. 2008, 120, 7464-7467
82. Angew. Chem. Int. Ed. 2008, 47, 7354-7357
83. E. Soriano, J. Marco-Contelles, Acc. Chem. Res. 2009, 42, 1026-1036
84. A. S. K. Hashmi, W. Yang, F. Rominger, Chem. Eur. J. 2012, 18, 6576-6580
85. A. S. K. Hashmi, W. Yang, F. Rominger, Angew. Chem. 2011, 123, 5882-5885
86. Angew. Chem. Int. Ed. 2011, 50, 5762-5765.
87. B. Crone, S. F. Kirsch, Chem. Eur. J. 2008, 14, 3514-3522
88. A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2007, 119, 5287-5289
89. Angew. Chem. Int. Ed. 2007, 46, 5195-5197
90. I. Alonso, B. Trillo, F. Lõpez, S. Montserrat, G. Ujaque, L. Castedo, A. Lledõs, J. L. Mascareñas, J. Am. Chem. Soc. 2009, 131, 13020-13030
91. A. S. K. Hashmi, M. Wieteck, I. Braun, M. Rudolph, F. Rominger, Angew. Chem. 2012, 124, 10785-10789
92. Angew. Chem. Int. Ed. 2012, 51, 10633-10637.
93. S. I. Kozhushkov, K. Wagner-Gillen, A. F. Khlebnikov, A. de Meijere, Synthesis 2010, 23, 3967-3973
94. S. Ma, Q. He, Tetrahedron 2006, 62, 2769-2778.
95. B. M. Trost, T. Yasukata, J. Am. Chem. Soc. 2001, 123, 7162-7163
96. L. F. Yao, Y. Wei, M. Shi, J. Org. Chem. 2009, 74, 9466-9469
97. F. Kleinbeck, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 9178-9179
98. C. Lim, J.-E. Kang, J.-E. Lee, S. Shin, Org. Lett. 2007, 9, 3539-3542
99. P. García-García, A. Martínez, A. M. Sanjuán, M. A. Fernández-Rodríguez, R. Sanz, Org. Lett. 2011, 13, 4970-4973
100. R. Chaudhuri, S. K. Pawar, K. Pati, R.-S. Liu, Adv. Synth. Catal. 2012, 354, 2241-2250.