Cascade palladium-catalyzed direct intramolecular arylation/alkene isomerization sequences: Synthesis of indoles and benzofurans

Angewandte Chemie - International Edition

Volumn 49, Issue 43, 2010, Pages 7958-7962

  Yagoubi, Myriam ^a   Cruz, Ana C F ^a   Nichols, Paula L ^b   Elliott, Richard L ^b   Willis, Michael C ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Benzofurans; Direct arylation reactions; Heterocycles; Indoles; Palladium

Indexed keywords

ARYLATION REACTIONS; BENZOFURANS; FUNCTIONALIZATIONS; HETEROCYCLES; INDOLES; SYNTHETIC ROUTES;

AROMATIC COMPOUNDS; CATALYSIS; ISOMERIZATION; OLEFINS; PALLADIUM; SYNTHESIS (CHEMICAL);

ISOMERS;

ALKENE; BENZOFURAN DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; ISOMERISM; SYNTHESIS;

ALKENES; BENZOFURANS; CATALYSIS; INDOLES; ISOMERISM; PALLADIUM;

EID: 78349257053     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004097     Document Type: Article

References (118)

1. Recent reviews
2. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
3. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
4. L. Ackermann, R. Vicente, A. Kapdi, Angew. Chem. 2009, 121, 9976
5. Angew. Chem. Int. Ed. 2009, 48, 9792
6. L. Ackermann, R. Vicente, Top. Curr. Chem. 2009, 292, 211
7. G. P. McGlacken, L. M. Bateman, Chem. Soc. Rev. 2009, 38, 2447
8. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
9. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
10. Angew. Chem. Int. Ed. 2009, 48, 5094
11. L. Ackermann, R. Vicente, in Modern Arylation Methods (Ed.:, L. Ackermann,), Wiley-VCH, Weinheim, 2009, pp. 311 - 333
12. B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949
13. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
14. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174.
15. Pioneering studies
16. D. E. Ames, D. Bull, Tetrahedron 1982, 38, 383
17. D. E. Ames, A. Opalko, Synthesis 1983, 234
18. Y. Akita, A. Inoue, K. Yamamoto, A. Ohta, T. Kurihara, M. Shimizu, Heterocycles 1985, 23, 2327
19. Y. Akita, Y. Itagaki, S. Takizawa, A. Ohta, Chem. Pharm. Bull. 1989, 37, 1477.
20. Selected recent examples
21. O. René, K. Fagnou, Org. Lett. 2010, 12, 2116
22. L. Ackermann, R. Vicente, Org. Lett. 2009, 11, 4922
23. O. René, D. Lapointe, K. Fagnou, Org. Lett. 2009, 11, 4560
24. Y. Wei, J. Kan, M. Wang, W. Su, M. Hong, Org. Lett. 2009, 11, 3346
25. O. Kobayashi, D. Uraguchi, T. Yamakawa, Org. Lett. 2009, 11, 2679
26. F. Vallée, J. J. Mousseau, A. B. Charette, J. Am. Chem. Soc. 2010, 132, 1514.
27. Selected recent examples
28. L. Ackermann, S. Barfüsser, J. Pospech, Org. Lett. 2010, 12, 724
29. L. Ackermann, R. Jeyachandran, H. K. Potukuchi, P. Novák, L. Büttner, Org. Lett. 2010, 12, 2056
30. S. A. Ohnmacht, A. J. Culshaw, M. F. Greaney, Org. Lett. 2010, 12, 224
31. F. Zhang, M. F. Greaney, Angew. Chem. 2010, 122, 2828
32. Angew. Chem. Int. Ed. 2010, 49, 2768
33. B. Liégault, I. Petrov, S. I. Gorelsky, K. Fagnou, J. Org. Chem. 2010, 75, 1047
34. J. Wen, S. Qin, L.-F. Ma, L. Dong, J. Zhang, S.-S. Liu, Y.-S. Duan, S.-Y. Chen, C.-W. Hu, X.-Q. Yu, Org. Lett. 2010, 12, 2694
35. I. Čerňa, R. Pohl, B. Klepetářová, M. Hocek, J. Org. Chem. 2010, 75, 2302
36. J. Huang, J. Chan, Y. Chen, C. J. Borths, K. D. Baucom, R. D. Larsen, M. M. Faul, J. Am. Chem. Soc. 2010, 132, 3674
37. M. pulák, R. Lubojack , P. enel, J. Kune , M. Pour, J. Org. Chem. 2010, 75, 241
38. M. Wasa, B. T. Worrell, J.-Q. Yu, Angew. Chem. 2010, 122, 1297
39. Angew. Chem. Int. Ed. 2010, 49, 1275
40. D. A. Candito, M. Lautens, Angew. Chem. 2009, 121, 6841
41. Angew. Chem. Int. Ed. 2009, 48, 6713
42. M. P. Huestis, K. Fagnou, Org. Lett. 2009, 11, 1357
43. D. J. Schipper, M. El-Salfiti, C. J. Whipp, K. Fagnou, Tetrahedron 2009, 65, 4977
44. L.-C. Campeau, D. R. Stuart, J.-P. Leclerc, M. Bertrand-Laperle, E. Villemure, H.-Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, K. Fagnou, J. Am. Chem. Soc. 2009, 131, 3291
45. B. Liégault, D. Lapointe, L. Caron, A. Vlassova, K. Fagnou, J. Org. Chem. 2009, 74, 1826
46. D. J. Schipper, L.-C. Campeau, K. Fagnou, Tetrahedron 2009, 65, 3155
47. L. Ackermann, R. Born, R. Vicente, ChemSusChem 2009, 2, 546
48. L. Ackermann, A. Althammer, S. Fenner, Angew. Chem. 2009, 121, 207
49. Angew. Chem. Int. Ed. 2009, 48, 201
50. L. Ackermann, S. Barfü er, Synlett 2009, 808
51. J. Cornella, P. Lu, I. Larrosa, Org. Lett. 2009, 11, 5506
52. T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 3072
53. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 1737
54. J. Roger, F. Po gan, H. Doucet, J. Org. Chem. 2009, 74, 1179
55. R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593.
56. Examples of transition metal-catalyzed direct arylation of alkenyl (pseudo)halides
57. M. R. Albicker, N. Cramer, Angew. Chem. 2009, 121, 9303
58. Angew. Chem. Int. Ed. 2009, 48, 9139
59. A. C. F. Cruz, N. D. Miller, M. C. Willis, Org. Lett. 2007, 9, 4391
60. C. C. Hughes, D. Trauner, Tetrahedron 2004, 60, 9675
61. C. C. Hughes, D. Trauner, Angew. Chem. 2002, 114, 1639
62. Angew. Chem. Int. Ed. 2002, 41, 1569
63. M. C. Willis, C. K. Claverie, M. F. Mahon, Chem. Commun. 2002, 832.
64. Examples of transition metal-catalyzed direct arylation of alkyl (pseudo)halides
65. M. Wasa, J.-Q. Yu, Tetrahedron 2010, 66, 4811
66. L. Ackermann, P. Novák, R. Vicente, N. Hofmann, Angew. Chem. 2009, 121, 6161
67. Angew. Chem. Int. Ed. 2009, 48, 6045
68. L. Ackermann, P. Novák, Org. Lett. 2009, 11, 4966
69. D. Lapointe, K. Fagnou, Org. Lett. 2009, 11, 4160
70. M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 9886
71. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, Angew. Chem. 2009, 121, 6213
72. Angew. Chem. Int. Ed. 2009, 48, 6097
73. C. Verrier, C. Hoarau, F. Marsais, Org. Biomol. Chem. 2009, 7, 647
74. S. J. Hwang, S. H. Cho, S. Chang, J. Am. Chem. Soc. 2008, 130, 16158
75. E. J. Hennessy, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 12084.
76. Recent reviews
77. F. Bellina, R. Rossi, Tetrahedron 2009, 65, 10269
78. L. Joucla, L. Djakovitch, Adv. Synth. Catal. 2009, 351, 673
79. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
80. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173.
81. For a review, see:, P. Thansandote, M. Lautens, Chem. Eur. J. 2009, 15, 5874; see also Ref. [4].
82. Notable exceptions include the construction of carbazole, dibenzofuran, and related systems, in which two tethered aromatic units undergo C-C bond formation by a direct arylation step. Selected examples
83. C. Wang, I. Piel, F. Glorius, J. Am. Chem. Soc. 2009, 131, 4194
84. T. Watanabe, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem. 2009, 74, 4720
85. J. K. Laha, P. Petrou, G. D. Cuny, J. Org. Chem. 2009, 74, 3152
86. R. B. Bedford, M. Betham, J. P. H. Charmant, A. L. Weeks, Tetrahedron 2008, 64, 6038
87. R. B. Bedford, M. Betham, J. Org. Chem. 2006, 71, 9403
88. J. Zhao, R. C. Larock, J. Org. Chem. 2006, 71, 5340
89. L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581
90. M. Parisien, D. Valette, K. Fagnou, J. Org. Chem. 2005, 70, 7578
91. J. Zhao, R. C. Larock, Org. Lett. 2005, 7, 701
92. L.-C. Campeau, P. Thansandote, K. Fagnou, Org. Lett. 2005, 7, 1857
93. T. Harayama, Heterocycles 2005, 65, 697
94. Q. H. Huang, A. Fazio, G. X. Dai, M. A. Campo, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 7460
95. Z. J. Liu, R. C. Larock, Org. Lett. 2004, 6, 3739
96. M. A. Campo, Q. H. Huang, T. L. Yao, Q. P. Tian, R. C. Larock, J. Am. Chem. Soc. 2003, 125, 11506
97. Y. M. Zhang, T. Razler, P. F. Jackson, Tetrahedron Lett. 2002, 43, 8235
98. R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2002, 2310
99. T. Iwaki, A. Yasuhara, T. Sakamoto, J. Chem. Soc. Perkin Trans. 1 1999, 1505.
100. For an elegant indole/carbazole synthesis based on the route disconnection that employs a cascade amination/ direct arylation sequence, see
101. L. Ackermann, A. Althammer, P. Mayer, Synthesis 2009, 3493
102. L. Ackermann, A. Althammer, Angew. Chem. 2007, 119, 1652
103. Angew. Chem. Int. Ed. 2007, 46, 1627.
104. Examples of alkenyl (pseudo)halide amination
105. M. C. Willis, G. N. Brace, Tetrahedron Lett. 2002, 43, 9085
106. J. Barluenga, M. A. Fernádez, F. Aznar, C. Valdés, Chem. Commun. 2002, 2362.
107. Conveniently prepared by halogenation/elimination of the corresponding enones, for example:, R. K. Dieter, L. E. Nice, S. E. Velu, Tetrahedron Lett. 1996, 37, 2377.
108. D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438
109. Angew. Chem. Int. Ed. 2008, 47, 6338.
110. J. A. Murphy, K. A. Scott, R. S. Sinclair, C. G. Martin, A. R. Kennedy, N. Lewis, J. Chem. Soc. Perkin Trans. 1 2000, 2395.
111. For mechanistic discussions, see
112. S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 10848
113. H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879
114. D. Garcia-Cuadrado, P. de Mendoza, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2007, 129, 6880
115. D. Garcia-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066
116. M. LaFrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16496
117. C.-H. Park, V. Ryabova, I. V. Seregin, A. W. Sromek, V. Gevorgyan, Org. Lett. 2004, 6, 1159
118. A. M. Echavarren, B. Gómez-Lor, J. J. González, . de Frutos, Synlett 2003, 583.