Palladium-catalyzed sonogashira-coupling conjoined C-H activation: A regioselective tandem strategy to access indolo- and pyrrolo[1,2- a ]quinolines

Journal of Organic Chemistry

Volumn 77, Issue 22, 2012, Pages 10382-10392

  Shukla, Satya Prakash ^a   Tiwari, Rakesh K ^a,b   Verma, Akhilesh K ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BOND FORMATION; C-H ACTIVATION; CYCLIZED PRODUCTS; PALLADIUM-CATALYZED; PYRROLO[1 ,2-A]QUINOLINES; REGIO-SELECTIVE; SIMPLE APPROACH; SONOGASHIRA COUPLING; SYNTHETIC METHODOLOGY;

ACETYLENE; ACTIVATION ANALYSIS; BIOACTIVITY; FUNCTIONAL GROUPS; REGIOSELECTIVITY;

CATALYSIS;

ALKYNE; BENZENE DERIVATIVE; BROMINE DERIVATIVE; FUNCTIONAL GROUP; INDOLE DERIVATIVE; PALLADIUM; PYRROLO[1,2 A]QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; HYDROGEN BOND; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; SONOGASHIRA REACTION; STEREOCHEMISTRY;

ALKYNES; CATALYSIS; CYCLIZATION; HYDROGEN BONDING; IMIDAZOLES; INDOLES; MOLECULAR STRUCTURE; PALLADIUM; PYRROLES; QUINOLINES; STEREOISOMERISM;

EID: 84869200569     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302112a     Document Type: Article

References (114)

1. Cadierno, V.; Crochet, P.; Francos, J.; Garcia-Garrido, S. E.; Gimeno, J.; Nebra, N. Green Chem. 2009, 11, 1992
2. Hirano, K.; Piel, I.; Glorius, F. Chem. Lett. 2011, 40, 786
3. Krompiec, S.; Krompiec, M.; Penczek, R.; Ignasiak, H. Coord. Chem. Rev. 2008, 252, 1819
4. Perez-Temprano, M. H.; Casares, J. A.; Espinet, P. Chem.-Eur. J. 2012, 18, 1864
5. Zhou, J. Chem.-Asian J. 2010, 5, 422
6. Ahlsten, N.; Bartoszewicz, A.; Martin-Matute, B. Dalton Trans. 2012, 41, 1660
7. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127
8. Ramirez, J.; Lillo, V.; Segarra, A. M.; Fernandez, E. Curr. Org. Chem. 2008, 12, 405
9. Wu, Y.-J. In Buchner Reaction; John Wiley & Sons, Inc.: Hoboken, NJ, 2010; p 424.
10. Zanardi, A.; Mata, J. A.; Peris, E. J. Am. Chem. Soc. 2009, 131, 14531
11. Smith, A. M. R.; Hii, K. K. Chem. Rev. 2011, 111, 1637
12. Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994
13. Schreiber, S. L. Science 2000, 287, 1964
14. Arya, P.; Chou, D. T. H.; Baek, M. G. Angew. Chem., Int. Ed. 2001, 40, 339
15. Walsh, D. P.; Chang, Y. T. Chem. Rev. 2006, 106, 2476
16. Breinbauer, R.; Vetter, I. R.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 2878
17. Dandapani, S.; Marcaurelle, L. A. Curr. Opin. Chem. Biol. 2010, 14, 362
18. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644
19. Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, PR215
20. Hamada, Y. Chem. Pharm. Bull. 2012, 60, 1
21. Catellani, M. In Arene Substitution Involving Temporary Incorporation and Removal of Carbon Tethers via Carbopalladation and Decarbopalladation; John Wiley & Sons, Inc.: Hoboken, NJ, 2002; Vol. 1, p 1479.
22. Hartwig, J. F. In Palladium-Catalyzed Synthesis of Aryl Ethers and Related Compounds Containing S and Se; John Wiley & Sons, Inc.: Hoboken, NJ, 2002; Vol. 1, p 1097.
23. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147 and references therein
24. Worlikar, S. A.; Larock, R. C. Org. Lett. 2009, 11, 2413
25. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Perboni, A.; Sferrazza, A.; Stabile, P. Org. Lett. 2010, 12, 3279
26. Seel, S.; Thaler, T.; Takatsu, K.; Zhang, C.; Zipse, H.; Straub, B. F.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2011, 133, 4774
27. Della, C. N.; Motti, E.; Mega, A.; Catellani, M. Adv. Synth. Catal. 2010, 352, 1451
28. Ackermann, L.; Sandmann, R.; Song, W. Org. Lett. 2011, 13, 1784
29. Motti, E.; Faccini, F.; Ferrari, I.; Catellani, M.; Ferraccioli, R. Org. Lett. 2006, 8, 3967
30. Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 14800
31. Cho, C.-H.; Jung, D.-I.; Neuenswander, B.; Larock, R. C. ACS Comb. Sci. 2011, 13, 501
32. Majumdar, K. C.; De, N.; Sinha, B.; Roy, B. Monatsh. Chem. 2012, 143, 1067
33. Majumdar, K. C.; Samanta, S.; Sinha, B. Synthesis 2012, 44, 817
34. Alberico, D.; Paquin, J.-F.; Lautens, M. Tetrahedron 2005, 61, 6283
35. Alberico, D.; Rudolph, A.; Lautens, M. J. Org. Chem. 2007, 72, 775
36. Thansandote, P.; Gouliaras, C.; Turcotte-Savard, M.-O.; Lautens, M. J. Org. Chem. 2009, 74, 1791
37. Schulman, J. M.; Friedman, A. A.; Panteleev, J.; Lautens, M. Chem. Commun. 2012, 48, 55
38. Newman, S. G.; Howell, J. K.; Nicolaus, N.; Lautens, M. J. Am. Chem. Soc. 2011, 133, 14916
39. Laleu, B.; Lautens, M. J. Org. Chem. 2008, 73, 9164
40. Fayol, A.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 4203
41. Blaszykowski, C.; Aktoudianakis, E.; Alberico, D.; Bressy, C.; Hulcoop, D. G.; Jafarpour, F.; Joushaghani, A.; Laleu, B.; Lautens, M. J. Org. Chem. 2008, 73, 1888
42. Newman, S. G.; Aureggi, V.; Bryan, C. S.; Lautens, M. Chem. Commun. 2009, 5236
43. Ackermann, L.; Althammer, A.; Mayer, P. Synthesis 2009, 3493
44. Ackermann, L. Angew. Chem., Int. Ed. 2011, 50, 3842
45. Ackermann, L.; Kapdi, A. R.; Fenner, S.; Kornhaaß, C.; Schulzke, C. Chem.-Eur. J. 2011, 17, 2965
46. Ackermann, L.; Kornhaass, C.; Zhu, Y. Org. Lett. 2012, 14, 1824
47. Ackermann, L.; Mehta, V. P. Chem.-Eur. J. 2012, 18, 10230
48. Lavrado, J.; Moreira, R.; Paulo, A. Curr. Med. Chem. 2010, 17, 2348
49. Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. S. V., Eds.; Pergamon Press: New York, 1996; Vol. 2, pp 207 - 257.
50. Le Quesne, P. W.; Dong, Y.; Blythe, T. A. Alkaloids: Chem. Biol. Perspect. 1999, 13, 237-287
51. Janosik, T.; Bergman, J. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Amsterdam, 2003; Vol. 15, pp 140 - 166.
52. Hazra, A.; Mondal, S.; Maity, A.; Naskar, S.; Saha, P.; Paira, R.; Sahu, K. B.; Paira, P.; Ghosh, S.; Sinha, C.; Samanta, A.; Banerjee, S.; Mondal, N. B. Eur. J. Med. Chem. 2011, 46, 2132
53. Kemnitzer, W.; Kuemmerle, J.; Jiang, S. C.; Sirisoma, N.; Kasibhatla, S.; Crogan-Grundy, C.; Tseng, B.; Drewe, J.; Cai, S. X. Bio. Med. Chem. Lett. 2009, 19, 3481
54. Ahmed, E.; Briseno, A. L.; Xia, Y.; Jenekhe, S. A. J. Am. Chem. Soc. 2008, 130, 1118
55. Zhu, L.; Kim, E.-G.; Yi, Y.; Ahmed, E.; Jenekhe, S. A.; Coropceanu, V.; Brédas, J.-L. J. Phys. Chem. C 2010, 114, 20401
56. Cram, D. J. Nature 1992, 356, 29
57. Schwartz, E. B.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1992, 114, 10775
58. Dijkstra, P. J.; Skowronska-Ptasinska, M.; Reinhoudt, D. N.; Den Hertog, H. J.; Van Eerden, J.; Harkema, S.; De Zeeuw, D. J. Org. Chem. 1987, 52, 4913
59. Chandrasekhar, S. Advances in Liquid Crystals; Academic Press: New York, 1982; Vol. 5, p 47.
60. Chandrasekhar, S.; Ranganath, G. S. Rep. Prog. Phys. 1990, 53, 57
61. Praefcke, K.; Kohne, B.; Singer, D. Angew. Chem., Int. Ed. 1990, 29, 177
62. Veber, D. F.; Strachan, R. G.; Bergstrand, S. J.; Holly, F. W.; Homnick, C. F.; Hirschmann, R.; Torchiana, M. L.; Saperstein, R. J. Am. Chem. Soc. 1976, 98, 2367
63. Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelley, J. W. J. Am. Chem. Soc. 1994, 116, 3988
64. Chai, D. I.; Lautens, M. J. Org. Chem. 2009, 74, 3054
65. Hulcoop, D. G.; Lautens, M. Org. Lett. 2007, 9, 1761
66. Baik, C.; Kim, D.; Kang, M. S.; Song, K.; Kang, S. O.; Ko, J. Tetrahedron 2009, 65, 5302
67. Schultz, D. M.; Wolfe, J. P. Org. Lett. 2010, 12, 1028
68. Takaya, J.; Udagawa, S.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2008, 47, 4906
69. Ohsawa, A.; Kawaguchi, T.; Igeta, H. Synthesis 1983, 1037
70. Wald, K. M.; Nada, A. A.; Szildágyi, G.; Wamhoff, H. Chem. Ber. 1980, 113, 2884
71. Panteleev, J.; Geyer, K.; Aguilar-Aguilar, A.; Wang, L.; Lautens, M. Org. Lett. 2010, 12, 5092
72. Lee, H. S.; Kim, S. H.; Kim, Y. M.; Kim, J. N. Tetrahedron Lett. 2010, 51, 5071
73. Verma, A. K.; Kesharwani, T.; Singh, J.; Tandon, V.; Larock, R. C. Angew.Chem., Int. Ed. 2009, 48, 1138
74. Verma, A. K.; Shukla, S. P.; Singh, J.; Rustagi, V. J. Org. Chem. 2011, 76, 5670
75. Chen, Y.; Cho, C.-H.; Larock, R. C. Org. Lett. 2009, 11, 173
76. Chen, Y.; Cho, C.-H.; Shi, F.; Larock, R. C. J. Org. Chem. 2009, 74, 6802
77. Cho, C.-H.; Jung, D.-I.; Larock, R. C. Tetrahedron Lett. 2010, 51, 6485
78. Cho, C.-H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 941
79. Chen, Z.; Yang, X.; Wu, J. Chem. Commun. 2009, 3469
80. Ye, S.; Wang, H.; Wu, J. Tetrahedron 2011, 67, 4628
81. Ding, Q.; Wang, Z.; Wu, J. J. Org. Chem. 2009, 74, 921
82. Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 15720
83. Huo, Z.; Tomeba, H.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 5531
84. Yang, F.; Jin, T.; Bao, M.; Yamamoto, Y. Tetrahedron 2011, 67, 10147
85. Yang, F.; Jin, T.; Bao, M.; Yamamoto, Y. Chem. Commun. 2011, 47, 4013
86. Just, Z. W.; Larock, R. C. J. Org. Chem. 2008, 73, 2662
87. Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141
88. Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937
89. Zhao, J.; Li, P.; Wu, C.; Chen, H.; Ai, W.; Sun, R.; Ren, H.; Larock, R. C.; Shi, F. Org. Biomol. Chem. 2012, 10, 1922
90. Rogness, D. C.; Larock, R. C. Tetrahedron Lett. 2009, 50, 4003
91. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689
92. Zhang, H.; Larock, R. C. Org. Lett. 2002, 4, 3035
93. Larock, R. C. Pure Appl. Chem. 1999, 71, 1435
94. Larock, R. C.; Tian, Q. J. Org. Chem. 1998, 63, 2002
95. Ackermann, L.; Lygin, A. V.; Hofmann, N. Org. Lett. 2011, 13, 3278
96. Ackermann, L.; Pospech, J.; Graczyk, K.; Rauch, K. Org. Lett. 2012, 14, 930
97. Thirunavukkarasu, V. S.; Donati, M.; Ackermann, L. Org. Lett. 2012, 14, 3416
98. Asao, N.; Sato, K.; Menggenbateer; Yamamoto, Y. J. Org. Chem. 2005, 70, 3682
99. Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412
100. Heller, S. T.; Natarajan, S. R. Org. Lett. 2007, 9, 4947
101. Patil, N. T.; Mutyala, A. K.; Lakshmi, P. G. V. V; Raju, P. V. K.; Sridhar, B. Eur. J. Org. Chem. 2010, 1999
102. Sahoo, A. K.; Mori, S.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 7972
103. Rustagi, V.; Aggarwal, T.; Verma, A. K. Green Chem. 2011, 13, 1640
104. Verma, A. K.; Jha, R. R.; Sankar, V. K.; Aggarwal, T.; Singh, R. P.; Chandra, R. Eur. J. Org. Chem. 2011, 6998
105. Shukla, S. P.; Tiwari, R.; Verma, A. K. Tetrahedron 2012, 68, 9035
106. Joshi, M.; Patel, M.; Tiwari, R.; Verma, A. K. J. Org. Chem. 2012, 77, 5633
107. Verma, A. K.; Rustagi, V.; Aggarwal, T.; Singh, A. P. J. Org. Chem. 2010, 75, 7691
108. Tiwari, R. K.; Singh, J.; Singh, D.; Verma, A. K.; Chandra, R. Tetrahedron 2005, 61, 9513
109. Verma, A. K.; Singh, J.; Sankar, V. K.; Chaudhary, R.; Chandra, R. Tetrahedron Lett. 2007, 48, 4207
110. Verma, A. K.; Singh, J.; Larock, R. C. Tetrahedron 2009, 65, 8434
111. Joshi, M.; Tiwari, R.; Verma, A. K. Org. Lett. 2012, 14, 1106
112. Rustagi, V.; Tiwari, R.; Verma, A. K. Eur. J. Org. Chem. 2012, 4590
113. Verma, A. K.; Jha, R. R.; Chaudhary, R.; Tiwari, R. K.; Reddy, K. S. K.; Danodia, A. J. Org. Chem. 2012, 77, 8191
114. Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 62, 7536