Functionalization of the 3-position of thiophene and benzo[b]thiophene moieties by palladium-catalyzed C-C bond forming reactions using diazonium salts

Advanced Synthesis and Catalysis

Volumn 353, Issue 11-12, 2011, Pages 2003-2012

  Raduán, Mõnica ^a   Padrosa, Joaquim ^a   Pla Quintana, Anna ^a   Parella, Teodor ^b   Roglans, Anna ^a  

^a UNIVERSITY OF GIRONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

benzo b thiophenes; diazonium salts; Matsuda Heck reactions; palladium; Suzuki Miyaura cross couplings; thiophenes

Indexed keywords

EID: 80051989568     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100226     Document Type: Article

References (120)

1. S. Gronowitz, in: The Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Vol. 44, Parts 1-5, (Ed.:, S. Gronowitz,), Wiley, New York, 1991
2. T. Eicher, S. Hauptmann, A. Speicher, in: The Chemistry of Heterocycles, Chapter 5, Section 5.6., Wiley-VCH, New York, 2003
3. Heterocyclic Chemistry, (Eds.:, J. A. Joule, K. Mills,), Blackwell Science Malden, MA, 2000.
4. For selected recent examples, see
5. C. Wu, E. R. Decker, N. Blok, H. Bui, T. J. You, J. Wang, A. R. Bourgoyne, V. Knowles, K. L. Berens, G. W. Holland, T. A. Brock, R. A. F. Dixon, J. Med. Chem. 2004, 47, 1969-1986
6. K. Doré, S. Dubus, H.-A. Ho, I. Lévesque, M. Brunette, G. Corbeil, M. Boissinot, G. Boivin, M. G. Bergeron, D. Boudreau, M. Leclerc, J. Am. Chem. Soc. 2004, 126, 4240-4244
7. R. Scarpelli, A. Di Marco, F. Ferrigno, R. Laufer, I. Marcucci, E. Muraglia, J. M. Ontoria, M. Rowley, S. Serafini, C. Steinkühler, P. Jones, Bioorg. Med. Chem. Lett. 2008, 18, 6078-6082
8. E. Muraglia, S. Altamura, D. Branca, O. Cecchetti, F. Ferrigno, M. V. Orsale, M. C. Palumbi, M. Rowley, R. Scarpelli, C. Steinkühler, P. Jones, Bioorg. Med. Chem. Lett. 2008, 18, 6083-6087
9. A. Åslund, C. J. Sigurdson, T. Klingstedt, S. Grathwohl, T. Bolmont, D. L. Dickstein, E. Glimsdal, S. Prokop, M. Lindgren, P. Konradsson, D. M. Holtzman, P. R. Hof, F. L. Heppner, S. Gandy, M. Jucker, A. Aguzzi, P. Hammarström, K. P. R. Nilsson, ACS Chem. Biol. 2009, 4, 673-684
10. S. Nomura, S. Sakamaki, M. Hongu, E. Kawanishi, Y. Koga, T. Sakamoto, Y. Yamamoto, K. Ueta, H. Kimata, K. Nakayama, M. Tsuda-Tsukimoto, J. Med. Chem, 2010, 53, 6355-6360.
11. K. Koike, Z. Jia, T. Nikaido, Y. Liu, Y. Zhao, D. Guo, Org. Lett. 1999, 1, 197-198.
12. For selected recent examples, see
13. H. Yu, A. E. Pullen, M. G. Büschel, T. M. Swager, Angew. Chem. 2004, 116, 3786-3789
14. Angew. Chem. Int. Ed. 2004, 43, 3700-3703
15. A. R. Murphy, J. Liu, C. Luscombe, D. Kavulak, J. M. J. Fréchet, R. J. Kline, M. D. McGehee, Chem. Mater. 2005, 17, 4892-4899
16. S. Kim, J. K. Lee, S. O. Kang, J. Ko, J.-H. Yum, S. Fantacci, F. De Angelis, D. Di Censo, M. K. Nazeeruddin, M. Grätzel, J. Am. Chem. Soc. 2006, 128, 16701-16707
17. N. Koumura, Z.-S. Wang, S. Mori, M. Miyashita, E. Suzuki, K. Hara, J. Am. Chem. Soc. 2006, 128, 14256-14257
18. M. Funahashi, F. Zhang, N. Tamaoki, Adv. Mater. 2007, 19, 353-358
19. C. D. McTiernan, K. Omri, M. Chahma, J. Org. Chem. 2010, 75, 6096-6103
20. R. Rieger, D. Beckmann, A. Mavrinskiy, M. Kastler, K. Müllen, Chem. Mater. 2010, 22, 5314-5318
21. T.-L. Choi, K.-M. Han, J.-I. Park, D. H. Kim, J.-M. Park, S. Lee, Macromolecules 2010, 43, 6045-6049
22. A. R. Mohebbi, F. Wudl, Chem. Eur. J. 2011, 17, 2642-2646.
23. For reviews, see
24. B. H. Lipshutz, Chem. Re v. 1986, 86, 795-819
25. G. Rassu, F. Zanardi, L. Battistini, G. Casiraghi, Chem. Soc. Re v. 2000, 29, 109-118.
26. For reviews, see
27. R. Chinchilla, C. Nájera, M. Yus, Chem. Rev. 2004, 104, 2667-2722
28. I. Osaka, R. D. McCullough, Acc. Chem. Res. 2008, 41, 1202-1214.
29. For reviews of transition metal-catalyzed direct arylation of aromatics and heteroaromatics, see
30. L.-C. Campeau, K. Fagnou, Chem. Commun. 2006, 1253-1264
31. K. Godula, D. Sames, Science 2006, 312, 67-72
32. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200-205
33. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238
34. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173-1193
35. L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35-41
36. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013-3039
37. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196-5217
38. Angew. Chem. Int. Ed. 2009, 48, 5094-5115
39. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976-10011
40. Angew. Chem. Int. Ed. 2009, 48, 9792-9826
41. G. P. McGlacken, L. M. Bateman, Chem. Soc. Rev. 2009, 38, 2447-2464
42. F. Bellina, R. Rossi, Tetrahedron 2009, 65, 10269-10310
43. A. A. Kulkarni, O. Daugulis, Synthesis 2009, 4087-4109
44. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624-655
45. J. Roger, A. L. Gottumukkala, H. Doucet, ChemCatChem 2010, 2, 20-40; for selected and recent examples of direct arylation of thiophene derivatives, see
46. F. Derridj, J. Roger, S. Djebbar, H. Doucet, Org. Lett. 2010, 12, 4320-4323
47. B. Liégault, I. Petrov, S. I. Gorelsky, K. Fagnou, J. Org. Chem. 2010, 75, 1047-1060
48. L. Chen, J. Roger, C. Bruneau, P. H. Dixneuf, H. Doucet, Chem. Commun. 2011, 47, 1782-1874
49. T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2011, 13, 706-708; for a report on direct beta arylation, see
50. K. Ueda, S. Yanagisawa, J. Yamaguchi, K. Itami, Angew. Chem. 2010, 122, 9130-9133
51. Angew. Chem. Int. Ed. 2010, 49, 8946-8949.
52. For monographies, see
53. Handbook of Organopalladium Chemistry for Organic Synthesis, Vols. 1 and 2, (Ed.:, E. Negishi,), Wiley-Interscience, Weinheim, 2002
54. Metal-Catalyzed Cross-Coupling Reactions, Vols. 1 and 2, (Ed.:, A. Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004
55. Transition Metals for Organic Synthesis, (Ed.:, M. Beller, C. Bolm,), Wiley-VCH, Weinheim, 2004
56. Palladacycles, Synthesis Characterization and Applications, (Eds.:, J. Dupont, M. Pfeffer,), Wiley-VCH, Weinheim, 2008
57. The Mizoroki-Heck Reaction, (Ed.:, M. Oestreich,), Wiley-VCH, 2009
58. J. J. Li, G. W. Gribble, in: Palladium in Heterocyclic Chemistry, Vol. 20, Tetrahedron Organic Chemistry Series, Pergamon, Oxford, 2000.
59. For selected recent examples, see
60. A. S. Karpov, F. Rominger, T. J. J. Müller, J. Org. Chem. 2003, 68, 1503-1511
61. S. Schröter, C. Stock, T. Bach, Tetrahedron 2005, 61, 2245-2267
62. K. Mitsudo, P. Thansandote, T. Wilhelm, B. Mariampillai, M. Lautens, Org. Lett. 2006, 8, 3939-3942
63. G. A. Molander, A. R. Brown, J. Org. Chem. 2006, 71, 9681-9686
64. R. J. Brea, M. P. Lõpez-Deber, L. Castedo, J. R. Granja, J. Org. Chem. 2006, 71, 7870-7873
65. K. L. Billingsley, K. W. Anderson, S. L. Buchwald, Angew. Chem. 2006, 118, 3564-3568
66. Angew. Chem. Int. Ed. 2006, 45, 3484-3488
67. K. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358-3366
68. A. S. Guram, X. Wang, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, J. Org. Chem. 2007, 72, 5104-5112
69. A. Begouin, S. Hesse, M.-J. R. P. Queiroz, G. Kirsch, Eur. J. Org. Chem. 2007, 1678-1682
70. N. Arai, T. Miyaoku, S. Teruya, A. Mori, Tetrahedron Lett. 2008, 49, 1000-1003
71. S. Sase, M. Jaric, A. Metzger, V. Malakhov, P. Knochel, J. Org. Chem. 2008, 73, 7380-7382
72. G. A. Molander, B. Canturk, L. E. Kennedy, J. Org. Chem. 2009, 74, 973-980
73. B. Bhayana, B. P. Fors, S. L. Buchwald, Org. Lett. 2009, 11, 3954-3957
74. T. Kinzel, Y. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 14073-14075.
75. K. Kikukawa, T. Matsuda, Chem. Lett. 1977, 159-162
76. K. Kikukawa, K. Nagira, T. Matsuda, Bull. Chem. Soc. Jpn. 1977, 50, 2207.
77. For a review, see
78. A. Roglans, A. Pla-Quintana, M. Moreno-Mañas, Chem. Rev. 2006, 106, 4622-4643. For two recent reviews of Matsuda-Heck reactions, see
79. J. G. Taylor, A. V. Moro, C. R. D. Correia, Eur. J. Org. Chem. 2011, 1403-1428, and references cited therein
80. F.-X. Felpin, L. Nassar-Hardy, F. Le Callonnec, E. Fouquet, Tetrahedron 2011, 67, 2815-2831, and references cited therein. For selected other recent examples, see
81. R. H. Taylor, F.-X. Felpin, Org. Lett. 2007, 9, 2911-2914
82. J. T. Kuethe, K. G. Childers, Adv. Synth. Catal. 2008, 350, 1577-1586
83. G. Bartoli, S. Cacchi, G. Fabrizi, A. Goggiamani, Synlett 2008, 2508-2512
84. F-.X. Felpin, E. Fouquet, Adv. Synth. Catal. 2008, 350, 863-868
85. B. Panda, T. K. Sarkar, Chem. Commun. 2010, 46, 3131-3133
86. G. Fabrizi, A. Goggiamani, A. Sferrazza, S. Cacchi, Angew. Chem. 2010, 122, 4161-4164
87. Angew. Chem. Int. Ed. 2010, 49, 4067-4070
88. T. Stern, S. Rückbrod, C. Czekelius, C. Donner, H. Brunner, Adv. Synth. Catal. 2010, 352, 1983-1992
89. F. Mo, D. Qiu, Y. Jiang, Y. Zhang, J. Wang, Tetrahedron Lett. 2011, 52, 518-522
90. S. Cacchi, G. Fabrizi, A. Goggiamani, A. Sferrazza, Org. Biomol. Chem. 2011, 9, 1727-1730
91. R. G. Kalkhambkar, K. K. Laali, Tetrahedron Lett. 2011, 52, 1733-1737.
92. For two Heck reactions of 3-aminopyridine, see
93. K. Kikukawa, K. Maemura, Y. Kiseki, F. Wada, T. Matsuda, C. S. Giam, J. Org. Chem. 1981, 46, 4885-4888. For two cases of Heck reaction with 2-methoxycarbonylthiophene-3-diazonium salts in which similar results to our own are obtained, see
94. E. Artuso, M. Barbero, I. Degani, S. Dughera, R. Fochi, Tetrahedron 2006, 62, 3146-3157
95. [11j]
96. C. Corral, A. Lasso, J. Lissavetzky, A. Sánchez Alvarez-Insúa, A. M. Valdeolmillos, Heterocycles 1985, 23, 1431-1435.
97. For recent reviews on potassium organotrifluoroborates, see
98. S. Darses, J. P. Genêt, Eur. J. Org. Chem. 2003, 4313-4327
99. G. A. Molander, R. Figueroa, Aldrichimica Acta 2005, 38, 49-56
100. G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275-286
101. H. A. Stefani, R. Cella, A. S. Vieira, Tetrahedron 2007, 63, 3623-3658
102. S. Darses, J.-P. Genêt, Chem. Rev. 2008, 108, 288-305
103. G. A. Molander, B. Canturk, Angew. Chem. 2009, 121, 9404-9425
104. Angew. Chem. Int. Ed. 2009, 48, 9240-9262.
105. S. Darses, T. Jeffery, J. L. Brayer, J. P. Demoute, J. P. Gênet, Bull. Soc. Chim. Fr. 1996, 133, 1095-1102
106. S. Darses, J. P. Gênet, J. L. Brayer, J. P. Demoute, Tetrahedron Lett. 1997, 38, 4393-4396
107. S. Darses, G. Michaud, J. P. Gênet, Eur. J. Org. Chem. 1999, 1875-1883.
108. J. Masllorens, I. González, A. Roglans, Eur. J. Org. Chem. 2007, 158-166.
109. J. R. Beck, J. Org. Chem. 1972, 37, 3224-3226.
110. T. Y. Zhang, J. O'tool, C. S. Proctor, J. Sulfur Chem. 1999, 22, 1-47
111. E. Campaigne, in: Comprehensive Heterocyclic Chemistry, Vol. 4, pp 863-934 (Eds.:, A. R. Katritzky, C. W. Rees,), Pergamon Press, Oxford, 1984
112. R. K. Russell, J. B. Press, in: Comprehensive Heterocyclic Chemistry II, Vol. 2, pp 679-729 (Eds.:, A. R. Katritzky, C. W. Rees, E. F. V. Scriven,), Pergamon Press, Oxford, 1996.
113. Modern Fluoroorganic Chemistry, (Ed.:, P. Kirsch,), Wiley-VCH, Weinheim, 2004
114. Organofluorine Chemistry: Principles and Commercial Applications, (Eds.:, R. E. Banks, B. E. Smart, J. C. Tatlow,), Plenium Press: New York, 1994
115. Handbook of Fluorous Chemistry, (Eds.:, J. A. Gladysz, D. P. Curran, I. T. Horváth,), Wiley-VCH, Weinheim, 2004.
116. T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2011, 13, 706-708.
117. J. M. Bastian, A. Ebnöther, E. Jucker, E. Rissi, A. P. Stoll, Helv. Chim. Acta 1971, 54, 277-282.
118. N. Gjos, S. Gronowitz, Arkiv. Foer Kemi 1968, 30, 225-232.
119. B. Bhayana, B. P. Fors, S. L. Buchwald, Org. Lett. 2009, 11, 3954-3957.
120. M. Miyasaka, K. Hirano, T. Satoh, M. Miura, Adv. Synth. Catal. 2009, 351, 2683-2688.