Synthesis of 2-Boryl- and silylindoles by copper-catalyzed borylative and silylative cyclization of 2-alkenylaryl isocyanides

Journal of Organic Chemistry

Volumn 75, Issue 14, 2010, Pages 4841-4847

  Tobisu, Mamoru ^a   Fujihara, Hirokazu ^a   Koh, Keika ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROSILANES; ISOCYANIDES; KINASE INHIBITORS; NEUTRAL CONDITIONS; QUINOXALINES; RAPID SYNTHESIS; RING SYSTEMS; ROOM TEMPERATURE; SUZUKI-MIYAURA REACTION;

COPPER; CYANIDES; FUNCTIONAL GROUPS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

2 HYDRIDEINDOLE; 2 SILYLINDOLE; ALKENYL GROUP; BORONIC ACID DERIVATIVE; COPPER; CYANIDE; INDOLE DERIVATIVE; PAULLONE; PHOSPHOTRANSFERASE INHIBITOR; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; ROOM TEMPERATURE; SILYLATION; SUZUKI REACTION;

EID: 77954545005     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101024f     Document Type: Article

References (135)

1. Selected recent reviews: Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
2. Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673
3. Selected reviews: Schreiber, S. L. Science 2000, 287, 1964
4. Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46
5. Spandl, R. J.; Bender, A.; Spring, D. R. Org. Biomol. Chem. 2008, 6, 1149
6. Selected reviews: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
7. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
8. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
9. Miura, T.; Murakami, M. Chem. Commun. 2007, 217
10. Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535
11. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461
12. Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2009, 48, 3565
13. Goossen, L. J.; Goossen, K.; Stanciu, C. Angew. Chem., Int. Ed. 2009, 48, 3569
14. Vazquez, E.; Davies, I. W.; Payack, J. F. J. Org. Chem. 2002, 67, 7551 and references therein.
15. For a review on catalytic borylation of C-H bonds, see: Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2009, 110, 890 Catalytic borylation of indoles
16. Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056
17. Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedron Lett. 2002, 43, 5649
18. Ishiyama, T.; Nobuta, Y.; Hartwig, J. F.; Miyaura, N. Chem. Commun. 2003, 2924
19. Mertins, K.; Zapf, A.; Beller, M. J. Mol. Catal. A: Chem. 2004, 207, 21
20. Tagata, T.; Nishida, M. Adv. Synth. Catal. 2004, 346, 1655
21. Paul, S.; Chotana, G. A.; Holmes, D.; Reichle, R. C.; Maleczka, R. E.; Smith, M. R. J. Am. Chem. Soc. 2006, 128, 15552
22. Kallepalli, V. A.; Shi, F.; Paul, S.; Onyeozili, E. N.; Maleczka, R. E.; Smith, M. R. J. Org. Chem. 2009, 74, 9199
23. Robbins, D. W.; Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 4068
24. Selected examples: Aimi, N.; Uchida, N.; Ohya, N.; Hosokawa, H.; H., T.; Sakai, S.-i.; Mendonza, L. A.; Polz, L.; Stöckigt, J. Tetrahedron Lett. 1991, 32, 4949
25. Williams, D. E.; Davies, J.; Patrick, B. O.; Bottriell, H.; Tarling, T.; Roberge, M.; Andersen, R. J. Org. Lett. 2008, 10, 3501
26. Shen, T. Y.; Winter, C. A. Adv. Drug Res. 1977, 12, 90
27. Schultz, C.; Link, A.; Leost, M.; Zaharevitz, D. W.; Gussio, R.; Sausville, E. A.; Meijer, L.; Kunick, C. J. Med. Chem. 1999, 42, 2909
28. Trotter, B. W.; Quigley, A. G.; Lumma, W. C.; Sisko, J. T.; Walsh, E. S.; Hamann, C. S.; Robinson, R. G.; Bhimnathwala, H.; Kolodin, D. G.; Zheng, W.; Buser, C. A.; Huber, H. E.; Lobell, R. B.; Kohl, N. E.; Williams, T. M.; Graham, S. L.; Dinsmore, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 865
29. Yang, Z.; Reiling, S.; Nieduzak, T. R.; Mathew, R. M.; Jackson, S.; Harris, K. J. PCT Int. Appl. WO 2008014186 Chem. Abstr. 2008, 148, 214951.
30. A seminal report: Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127 A review
31. Tokuyama, H.; Fukuyama, T. Chem. Rec. 2002, 2, 37
32. A review of indole synthesis from isocyanides: Campo, J.; Garciá-Valverde, M.; Marcaccini, S.; Rojo, M. J.; Torrroba, T. Org. Biomol. Chem. 2006, 4, 757
33. Niznik, G. E.; Morrison, W. H.; Walborsky, H. M. J. Org. Chem. 1974, 39, 600
34. Murakami, M.; Ito, H.; Ito, Y. J. Org. Chem. 1988, 53, 4158
35. Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977
36. Tobisu, M.; Yamaguchi, S.; Chatani, N. Org. Lett. 2007, 9, 3351
37. For an excellent introduction to nucleophilic boryl species, see: Segawa, Y.; Suzuki, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2008, 130, 16069
38. Dang, L.; Lin, Z.; Marder, T. B. Chem. Commun. 2009, 3987
39. Ito, H.; Yamanaka, H.; Tateiwa, J.-i.; Hosomi, A. Tetrahedron Lett. 2000, 41, 6821
40. Takahashi, K.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 29, 982
41. Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2001, 625, 47
42. Mun, S.; Lee, J.-E.; Yun, J. Org. Lett. 2006, 8, 4887
43. Lee, J.-E.; Yun, J. Angew. Chem., Int. Ed. 2008, 47, 145
44. Lee, J.-E.; Kwon, J.; Yun, J. Chem. Commun. 2008, 733
45. Lillo, V.; Prieto, A.; Bonet, A.; Díaz-Requejo, M. M.; Ramírez, J.; Párez, P. J.; Fernández, E. Organometallics 2008, 28, 659
46. Dang, L.; Lin, Z.; Marder, T. B. Organometallics 2008, 27, 4443
47. Sim, H.-S.; Feng, X.; Yun, J. Chem. - Eur. J. 2009, 15, 1939
48. Feng, X.; Yun, J. Chem. Commun. 2009, 6577
49. Lillo, V.; Bonet, A.; Fernández Dalton Trans. 2009, 2899
50. Chea, H.; Sim, H.-S.; Yun, J. Adv. Synth. Catal. 2009, 351, 855
51. Fleming, W. J.; Müller-Bunz, H.; Lillo, V.; Fernández, E.; Guiry, P. J. Org. Biomol. Chem. 2009, 7, 2520
52. Chen, I. H.; Yin, L.; Itano, W.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 11664
53. Schiffner, J. A.; Müther, K.; Oestreich, M. Angew. Chem., Int. Ed. 2010, 49, 1194
54. Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. J. Am. Chem. Soc. 2006, 128, 11036
55. McIntosh, M. L.; Moore, C. M.; Clark, T. B. Org. Lett. 2010, 12, 1996
56. Beenen, M. A.; An, C.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6910
57. Ramachandran, P. V.; Pratihar, D.; Biswas, D.; Srivastava, A.; Ram Reddy, M. V. Org. Lett. 2004, 6, 481
58. Ito, H.; Kawakami, C.; Sawamura, M. J. Am. Chem. Soc. 2005, 127, 16034
59. Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856
60. Ito, H.; Sasaki, Y.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 15774
61. Ito, H.; Kosaka, Y.; Nonoyama, K.; Sasaki, Y.; Sawamura, M. Angew. Chem., Int. Ed. 2008, 47, 7424
62. Ito, H.; Okura, T.; Matsuura, K.; Sawamura, M. Angew. Chem., Int. Ed. 2010, 49, 560
63. Ito, H.; Toyoda, T.; Sawamura, M. J. Am. Chem. Soc. 2010, 132, 5990
64. Styrenes: Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. Organometallics 2006, 25, 2405
65. Dang, L.; Zhao, H.; Lin, Z.; Marder, T. B. Organometallics 2007, 26, 2824
66. Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160 1,3-Dienes:
67. 2
68. Laitar, D. S.; Muller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196
69. Zhao, H.; Lin, Z.; Marder, T. B. J. Am. Chem. Soc. 2006, 128, 15637, Alkynes
70. Lee, Y.; Jang, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 18234
71. Kim, H. R.; Jung, I. G.; Yoo, K.; Jang, K.; Lee, E. S.; Yun, J.; Son, S. U. Chem. Commun. 2010, 758
72. The starting isocyanides used in this study can readily be prepared from the corresponding 2-iodoanilines. See the Supporting Information for details.
73. For the instability of 2-heteroarylboronic acids, see: Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358
74. Knapp, D. M.; Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2009, 131, 6961
75. A seminal report: Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918
76. See also ref 3b-3e.
77. Seminal reports: Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229
78. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579
79. See also ref 3b-3e.
80. For example, see: Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
81. For recent studies of biological activities of paullone families, see: Reichwald, C.; Shimony, O.; Dunkel, U.; Sacerdoti-Sierra, N.; Jaffe, C. L.; Kunick, C. J. Med. Chem. 2008, 51, 659
82. Stukenbrock, H.; Mussmann, R.; Geese, M.; Ferandin, Y.; Lozach, O.; Lemcke, T.; Kegel, S.; Lomow, A.; Burk, U.; Dohrmann, C.; Meijer, L.; Austen, M.; Kunick, C. J. Med. Chem. 2008, 51, 2196
83. Becker, A.; Kohfeld, S.; Lader, A.; Preu, L.; Pies, T.; Wieking, K.; Ferandin, Y.; Knockaert, M.; Meijer, L.; Kunick, C. Eur. J. Med. Chem. 2010, 45, 335
84. Egert-Schmidt, A.-M.; Dreher, J.; Dunkel, U.; Kohfeld, S.; Preu, L.; Weber, H.; Ehlert, J. E.; Mutschler, B.; Totzke, F.; Schächtele, C.; Kubbutat, M. H. G.; Baumann, K.; Kunick, C. J. Med. Chem. 2010, 53, 2433
85. Notes: It has been reported that tin-mediated paullone synthesis from 5a requires the use of N -protected iodoaniline and the overall yield is less efficient (43% from 5a). See: Henry, N.; Blu, J.; Bénéteau, V.; Mérour, J.-Y. Synthesis 2006, 22, 3895
86. Synthesis of paullone via the Suzuki-Miyaura coupling of in situ prepared 2-(2-boryl-1 H -indol-3-yl)acetonitrile has been reported, but the yield was low (25%). See: Baudoin, O.; Cesario, M.; Guenard, D.; Gueritte, F. J. Org. Chem. 2002, 67, 1199
87. Suginome, M.; Ito, Y. In Science of Synthesis; Murahashi, S.-I., Ed.; Thieme: Stuttgart, 2004; Vol. 19; pp 445 - 530.
88. For representative recent reports on the catalytic reaction involving CuH species generated from HB(pin), see: Lipshutz, B. H.; Boskovic, Z. V.; Aue, D. H. Angew. Chem., Int. Ed. 2008, 47, 10183
89. Du, Y.; Xu, L.-W.; Shimizu, Y.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 16146
90. Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int. Ed. 2009, 48, 6062
91. 3, see: Welle, A.; Díez- González, S.; Tinant, B.; Nolan, S. P.; Riant, O. Org. Lett. 2006, 8, 6059
92. Deutsch, C.; Lipshutz, B. H.; Krause, N. Angew. Chem., Int. Ed. 2007, 46, 1650
93. Yoo, K.; Kim, H.; Yun, J. Chem. - Eur. J. 2009, 15, 11134
94. Zhong, C.; Sasaki, Y.; Ito, H.; Sawamura, M. Chem. Commun. 2009, 5850
95. Rupnicki, L.; Saxena, A.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 10386
96. Ito, H.; Ishizuka, T.; Tateiwa, J.-i.; Sonoda, M.; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196
97. Clark, C. T.; Lake, J. F.; Scheidt, K. A. J. Am. Chem. Soc. 2003, 126, 84
98. Walter, C.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2006, 45, 5675
99. Walter, C.; Oestreich, M. Angew. Chem., Int. Ed. 2008, 47, 3818
100. Walter, C.; Fröhlich, R.; Oestreich, M. Tetrahedron 2009, 65, 5513
101. Ohmiya, H.; Ito, H.; Sawamura, M. Org. Lett. 2009, 11, 5618
102. Silylindoles via catalytic C-H bond silylation: Ishiyama, T.; Sato, K.; Nishio, Y.; Saiki, T.; Miyaura, N. Chem. Commun. 2005, 5065
103. Lu, B.; Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 7508 Preparation and cross-coupling of 2-indolylsilanols
104. Denmark, S. E.; Baird, J. D. Org. Lett. 2004, 6, 3649
105. Denmark, S. E.; Baird, J. D. Org. Lett. 2006, 8, 793
106. Denmark, S. E.; Baird, J. D.; Regens, C. S. J. Org. Chem. 2008, 73, 1440
107. Denmark, S. E.; Baird, J. D. Tetrahedron 2009, 65, 3120
108. During the preparation of this manuscript, a report on copper-catalyzed 1,4-addition of a silyl group in silylboronates to unsaturated carbonyls was published: Lee, K.-s.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 2898
109. 2, see: Uemura, T.; Chatani, N. J. Org. Chem. 2005, 70, 8631
110. Villalobos, J. M.; Srogl, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 15734
111. Zheng, H.; Zhang, Q.; Chen, J.; Liu, M.; Cheng, S.; Ding, J.; Wu, H.; Su, W. J. Org. Chem. 2008, 74, 943
112. Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2009, 48, 1114
113. Zhu, J.; Lin, Z.; Marder, T. B. Inorg. Chem. 2005, 44, 9384
114. Dioumaev, V. K.; Procopio, L. J.; Carroll, P. J.; Berry, D. H. J. Am. Chem. Soc. 2003, 125, 8043 and references therein.
115. Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2008, 130, 15254
116. Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2007, 46, 6710 and references therein.
117. Synthesis of pyridine derivatives via cyclization of isocyanides: Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127
118. Curran, D. P.; Liu, H.; Josien, H.; Ko, S. B. Tetrahedron 1996, 52, 11385
119. Josien, H.; Ko, S. B.; Bom, D.; Curran, D. P. Chem. - Eur. J. 1998, 4, 67
120. Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213
121. Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215
122. Lu, X.; Petersen, J. L.; Wang, K. K. Org. Lett. 2003, 5, 3277
123. Mitamura, T.; Tsuboi, Y.; Iwata, K.; Tsuchii, K.; Nomoto, A.; Sonoda, M.; Ogawa, A. Tetrahedron Lett. 2007, 48, 5953
124. Liu, L.; Wang, Y.; Wang, H.; Peng, C.; Zhao, J.; Zhu, Q. Tetrahedron Lett. 2009, 50, 6715
125. Mitamura, T.; Iwata, K.; Ogawa, A. Org. Lett. 2009, 11, 3422
126. See also refs 9c and 35.
127. 2Ph affords 2-boryl-3-silylquinoxaline. See: Suginome, M.; Fukuda, T.; Ito, Y. J. Organomet. Chem. 2002, 643-644, 508 For related polymerization, see
128. Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880
129. The mechanism for the formation of 21c is currently unclear. Since 21c was not observed when the reaction was conducted in the absence of Cu(OAc), 21c is formed through copper catalysis.
130. For our work on catalytic reactions using isocyanides, see: Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812
131. Oshita, M.; Yamashita, K.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 761
132. Yoshioka, S.; Oshita, M.; Tobisu, M.; Chatani, N. Org. Lett. 2005, 7, 3697
133. Tobisu, M.; Kitajima, A.; Yoshioka, S.; Hyodo, I.; Oshita, M.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 11431
134. Tobisu, M.; Ito, S.; Kitajima, A.; Chatani, N. Org. Lett. 2008, 10, 5223
135. See also ref 9d.