N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles

Angewandte Chemie - International Edition

Volumn 53, Issue 36, 2014, Pages 9603-9607

  Hovey, M Todd ^a   Check, Christopher T ^a   Sipher, Alexandra F ^a   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

asymmetric synthesis; carbenes; cooperative effects

Indexed keywords

CATALYSIS; ENZYME INHIBITION; QUINONE; TRANSITION METALS;

ASYMMETRIC SYNTHESIS; CARBENES; CATALYTIC SYNTHESIS; CATALYZED SYNTHESIS; CO-OPERATIVE EFFECTS; KINASE INHIBITORS; METAL-FREE SYNTHESIS; N-HETEROCYCLIC CARBENES;

SYNTHESIS (CHEMICAL);

CARBENE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; METHANE; PROTEIN KINASE INHIBITOR;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AZA COMPOUNDS; CATALYSIS; HETEROCYCLIC COMPOUNDS; INDOLES; METHANE; PROTEIN KINASE INHIBITORS; STEREOISOMERISM;

EID: 84906948906     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405035     Document Type: Article

References (108)

1. T. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761-793
2. A. J. Kochanowska-Karamyan, M. T. Hamann, Chem. Rev. 2010, 110, 4489-4497
3. S. Lal, T. J. Snape, Curr. Med. Chem. 2012, 19, 4828-4837
4. N. K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C. H. Kim, A. K. Verma, E. H. Choi, Molecules 2013, 18, 6620-6662.
5. R. Möhlau, Ber. Dtsch. Chem. Ges. 1881, 14, 171-175.
6. E. Fischer, F. Jourdan, Ber. Dtsch. Chem. Ges. 1883, 16, 2241-2245
7. E. Fischer, O. Hess, Ber. Dtsch. Chem. Ges. 1884, 17, 559-568.
8. T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 2001, 2491-2515
9. S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920
10. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911
11. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786-9824
12. Angew. Chem. Int. Ed. 2009, 48, 9608-9644
13. D. F. Taber, P. K. Tirunahari, Tetrahedron 2011, 67, 7195-7210
14. M. Platon, R. Amardeil, L. Djakovitch, J.-C. Hierso, Chem. Soc. Rev. 2012, 41, 3929-3968
15. N. Lebrasseur, I. Larrosa, Recent Advances in the C2 and C3 Regioselective Direct Arylation of Indoles, Vol. 105, Elsevier, Amsterdam, 2012
16. M. Inman, C. J. Moody, Chem. Sci. 2013, 4, 29-41.
17. C.-y. Chen, C. H. Senanayake, T. J. Bill, R. D. Larsen, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 3738-3741
18. B. A. Haag, Z.-G. Zhang, J.-S. Li, P. Knochel, Angew. Chem. 2010, 122, 9703-9706
19. Angew. Chem. Int. Ed. 2010, 49, 9513-9516
20. S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534-18537
21. M. Inman, A. Carbone, C. J. Moody, J. Org. Chem. 2012, 77, 1217-1232
22. A. Kuznetsov, A. Makarov, A. E. Rubtsov, A. V. Butin, V. Gevorgyan, J. Org. Chem. 2013, 78, 12144-12153.
23. V. Sridharan, S. Perumal, C. Avendaño, J. C. Menéndez, Synlett 2006, 91-95
24. Y. Vara, E. Aldaba, A. Arrieta, J. L. Pizarro, M. I. Arriortua, F. P. Cossío, Org. Biomol. Chem. 2008, 6, 1763-1772.
25. S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 10251-10263
26. A. Takeda, S. Kamijo, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 5662-5663
27. J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511
28. Angew. Chem. Int. Ed. 2003, 42, 2406-2409
29. K. R. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2003, 6, 79-82
30. A. Saito, A. Kanno, Y. Hanzawa, Angew. Chem. 2007, 119, 4005-4007
31. Angew. Chem. Int. Ed. 2007, 46, 3931-3933
32. B. M. Trost, A. McClory, Angew. Chem. 2007, 119, 2120-2123
33. Angew. Chem. Int. Ed. 2007, 46, 2074-2077
34. K. Cariou, B. Ronan, S. Mignani, L. Fensterbank, M. Malacria, Angew. Chem. 2007, 119, 1913-1916
35. Angew. Chem. Int. Ed. 2007, 46, 1881-1884
36. J. Barluenga, A. Jiménez-Aquino, C. Valdés, F. Aznar, Angew. Chem. 2007, 119, 1551-1554
37. Angew. Chem. Int. Ed. 2007, 46, 1529-1532
38. D. R. Stuart, M. g. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474-16475
39. S. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, F. Glorius, Angew. Chem. 2008, 120, 7340-7343
40. Angew. Chem. Int. Ed. 2008, 47, 7230-7233
41. M. Shen, B. E. Leslie, T. G. Driver, Angew. Chem. 2008, 120, 5134-5137
42. Angew. Chem. Int. Ed. 2008, 47, 5056-5059
43. Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y. Cui, N. Jiao, Angew. Chem. 2009, 121, 4642-4646
44. Angew. Chem. Int. Ed. 2009, 48, 4572-4576
45. R. Bernini, G. Fabrizi, A. Sferrazza, S. Cacchi, Angew. Chem. 2009, 121, 8222-8225
46. Angew. Chem. Int. Ed. 2009, 48, 8078-8081
47. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326-18339
48. B. J. Stokes, S. Liu, T. G. Driver, J. Am. Chem. Soc. 2011, 133, 4702-4705
49. K. Sun, S. Liu, P. M. Bec, T. G. Driver, Angew. Chem. 2011, 123, 1740-1744
50. Angew. Chem. Int. Ed. 2011, 50, 1702-1706
51. S. Cacchi, G. Fabrizi, A. Goggiamani, C. Molinaro, R. Verdiglione, J. Org. Chem. 2014, 79, 401-407.
52. R. C. Larock, E. K. Yum, J. Am. Chem. Soc. 1991, 113, 6689-6690
53. R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172-8174; for a review on the removal of toxic metal impurity, see
54. C. E. Garrett, K. Prasad, Adv. Synth. Catal. 2004, 346, 889-900; for palladium contamination in Larock syntheses, see
55. V. W. Rosso, D. A. Lust, P. J. Bernot, J. A. Grosso, S. P. Modi, A. Rusowicz, T. C. Sedergran, J. H. Simpson, S. K. Srivastava, M. J. Humora, N. G. Anderson, Org. Process Res. Dev. 1997, 1, 311-314; for examples of noncommercially available alkynes in Larock indole syntheses, see Ref. [4c] and references therein.
56. J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724
57. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416-5470
58. R. P. Wurz, Chem. Rev. 2007, 107, 5570-5595
59. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569
60. D. W. C. MacMillan, Nature 2008, 455, 304-308.
61. V. Nair, S. Bindu, V. Sreekumar, Angew. Chem. 2004, 116, 5240-5245
62. Angew. Chem. Int. Ed. 2004, 43, 5130-5135
63. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606-5655
64. N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046-3058
65. Angew. Chem. Int. Ed. 2007, 46, 2988-3000
66. V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev. 2008, 37, 2691-2698
67. E. M. Phillips, A. Chan, K. A. Scheidt, Aldrichimica Acta 2009, 42, 55-66
68. V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose, V. Sreekumar, Chem. Soc. Rev. 2011, 40, 5336-5346
69. X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511-3522
70. J. Douglas, G. Churchill, A. Smith, Synthesis 2012, 2295-2309
71. S. De Sarkar, A. Biswas, R. C. Samanta, A. Studer, Chem. Eur. J. 2013, 19, 4664-4678
72. S. J. Ryan, L. Candish, D. W. Lupton, Chem. Soc. Rev. 2013, 42, 4906-4917.
73. A. Reissert, Ber. Dtsch. Chem. Ges. 1897, 30, 1030-1053.
74. H. Stetter, A. Landscheidt, Chem. Ber. 1979, 112, 2419-2422
75. H. Stetter, W. Basse, J. Nienhaus, Chem. Ber. 1980, 113, 690-698
76. A. E. Mattson, A. R. Bharadwaj, K. A. Scheidt, J. Am. Chem. Soc. 2004, 126, 2314-2315.
77. Y. Li, F.-Q. Shi, Q.-L. He, S.-L. You, Org. Lett. 2009, 11, 3182-3185
78. Q. Y. Toh, A. McNally, S. Vera, N. Erdmann, M. J. Gaunt, J. Am. Chem. Soc. 2013, 135, 3772-3775; for a related, yet noncatalytic, NHC-mediated acyl anion addition to primary benzyl halides, see
79. L. Lin, Y. Li, W. Du, W.-P. Deng, Tetrahedron Lett. 2010, 51, 3571-3574; for the catalytic addition of NHC-mediated acyl anions to benzylic/activated alkyl halides, see
80. M. Padmanaban, A. T. Biju, F. Glorius, Org. Lett. 2011, 13, 98-101.
81. E. M. Burgess, L. McCullagh, J. Am. Chem. Soc. 1966, 88, 1580-1581
82. M. Ikeda, S. Matsugashita, F. Tabusa, H. Ishibashi, Y. Tamura, J. Chem. Soc. Chem. Commun. 1975, 575-576
83. M. Lancaster, D. J. H. Smith, J. Chem. Soc. Chem. Commun. 1980, 471-472
84. K. Wojciechowski, Tetrahedron 1993, 49, 7277-7286.
85. Y. Ito, S. Miyata, M. Nakatsuka, T. Saegusa, J. Am. Chem. Soc. 1981, 103, 5250-5251.
86. R. D. Bowen, D. E. Davies, C. W. G. Fishwick, T. O. Glasbey, S. J. Noyce, R. C. Storr, Tetrahedron Lett. 1982, 23, 4501-4504
87. E. Foresti, P. Spagnolo, P. Zanirato, J. Chem. Soc. Perkin Trans. 1 1989, 1354-1356
88. C. K. Lau, L. Trimble, A. S. Caille, J. M. Wiebe, Tetrahedron 1996, 52, 11705-11724
89. K. Nishiyama, H. Kubo, T. Sato, K. Higashiyama, S. Ohmiya, Heterocycles 1998, 48, 1103-1106.
90. H. Steinhagen, E. J. Corey, Angew. Chem. 1999, 111, 2054-2056
91. Angew. Chem. Int. Ed. 1999, 38, 1928-1931
92. F. Avemaria, S. Vanderheiden, S. Bräse, Tetrahedron 2003, 59, 6785-6796
93. Q.-Q. Yang, C. Xiao, L.-Q. Lu, J. An, F. Tan, B.-J. Li, W.-J. Xiao, Angew. Chem. 2012, 124, 9271-9274
94. Angew. Chem. Int. Ed. 2012, 51, 9137-9140
95. Q.-Q. Yang, Q. Wang, J. An, J.-R. Chen, L.-Q. Lu, W.-J. Xiao, Chem. Eur. J. 2013, 19, 8401-8404.
96. A. E. Mattson, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 4508-4509
97. H. Lv, L. You, S. Ye, Adv. Synth. Catal. 2009, 351, 2822-2826
98. J. Izquierdo, A. Orue, K. A. Scheidt, J. Am. Chem. Soc. 2013, 135, 10634-10637
99. H. Lv, W.-Q. Jia, L.-H. Sun, S. Ye, Angew. Chem. 2013, 125, 8769-8772
100. Angew. Chem. Int. Ed. 2013, 52, 8607-8610.
101. G. C. Vougioukalakis, R. H. Grubbs, J. Am. Chem. Soc. 2008, 130, 2234-2245
102. I. Piel, M. D. Pawelczyk, K. Hirano, R. Fröhlich, F. Glorius, Eur. J. Org. Chem. 2011, 5475-5484.
103. B. Cardinal-David, D. E. A. Raup, K. A. Scheidt, J. Am. Chem. Soc. 2010, 132, 5345-5347
104. D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766-771.
105. S. E. O'Toole, C. A. Rose, S. Gundala, K. Zeitler, S. J. Connon, J. Org. Chem. 2011, 76, 347-357
106. C. Rose, S. Gundala, S. Connon, K. Zeitler, Synthesis 2011, 190-198
107. C. A. Rose, S. Gundala, C.-L. Fagan, J. F. Franz, S. J. Connon, K. Zeitler, Chem. Sci. 2012, 3, 735-740.
108. "c-Kit Modulators and Methods of Use":, W. Cheng, E. W. Co, M. H. Kim, R. R. Klein, D. T. Le, A. Lew, J. M. Nuss, W. Xu, W. Bajjalieh, WIPO. WO 2005/020921A2. March 10, 2005.