Rhodium(III)-catalyzed cyclative capture approach to diverse 1-aminoindoline derivatives at room temperature

Angewandte Chemie - International Edition

Volumn 54, Issue 5, 2015, Pages 1657-1661

  Zhao, Dongbing ^a   Vásquez Céspedes, Suhelen ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

C H functionalization; Directing groups; Heterocycles; Indolines; Rhodium

Indexed keywords

ACTIVATION ANALYSIS; ADDITION REACTIONS; CATALYSIS; RHODIUM;

C-H ACTIVATION; C-H FUNCTIONALIZATION; CATALYTIC METHODS; DIRECTING GROUPS; HETEROCYCLES; INDOLINES; NUCLEOPHILIC ADDITIONS; RHODIUM (III);

RHODIUM COMPOUNDS;

ALKENE; CARBON; HYDROGEN; INDOLE DERIVATIVE; INDOLINE; RHODIUM;

CATALYSIS; CHEMISTRY; QUANTUM THEORY; TEMPERATURE;

ALKENES; CARBON; CATALYSIS; HYDROGEN; INDOLES; QUANTUM THEORY; RHODIUM; TEMPERATURE;

EID: 84921456036     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410342     Document Type: Article

References (96)

1. For selected examples, see: a) E. J. Glamkowski, P. A. Eieitano, J. Med. Chem. 1979, 22, 106
2. b) G. Cignarella, P. Sanna, J. Med. Chem. 1981, 24, 1003
3. c) H. H. Buschmann, A. Torrens Jover, J. Mas Prio, J. R. Quintana Ruiz, A. Dordal Zueras, WO2007009687A1
4. d) S. Thakrar, N. Pandya, H. Vala, A. Bavishi, A. Radadiya, C. Pannecouque, A. K. Shah, Chem. Biol. Interface 2012, 2, 107.
5. For selected examples, see: a) J. L. Stanton, M. H. Ackerman, J. Med. Chem. 1983, 26, 986
6. b) P. Melnyk, B. Legrand, J. Gasche, P. Ducrot, C. Thal, Tetrahedron 1995, 51, 1941
7. c) Y. H. Kim, J. Y. Choi, Tetrahedron Lett. 1996, 37, 5543
8. d) Y Kiryu, S. Itoh, K. Kaneko, H. Katayama, Chem. Pharm. Bull. 1998, 46, 1810
9. e) A. B. Smith III, L. Kuerti, A. H. Davulcu, Org. Lett. 2006, 8, 2167
10. f) S. Sakami, M. Maeda, K. Kawai, T. Aoki, K. Kawamura, H. Fujii, K. Hasebe, M. Nakajima, T. Endo, S. Ueno, T. Ito, J. Kamei, H. Nagase, J. Med. Chem. 2008, 51, 4404.
11. a) M. Elkhatib, L. Peyrot, R. Metz, R. Tenu, F. Elomar, H. Delalu, Int. J. Chem. Kinet. 2002, 34, 575
12. b) M. L. Kantor, US4564677A1.
13. For selected examples, see: a) J.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 6452
14. Angew. Chem. 2008, 120, 6552
15. b) J. L. Neumann, S. Rakshit, T. Drçge, F. Glorius, Angew. Chem. Int. Ed. 2009, 48, 6892
16. Angew. Chem. 2009, 121, 7024
17. c) D.-S. Wang, Q.-A. Chen, W. Li, C.-B. Yu, Y-G Zhou, X. Zhang, J. Am. Chem. Soc. 2010, 132, 8909
18. d) T.-S. Mei, D. Leow, H. Xiao, B. N. Laforteza, J.-Q. Yu, Org. Lett. 2013, 15, 3058.
19. Until now, only one intramolecular catalytic method has been reported to make 1-aminoindolines with very limited scope, see: K. Hasegawa, N. Kimura, S. Arai, A. Nishida, J. Org. Chem. 2008, 73, 6363.
20. a) T Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212
21. b) D. A. Colby, A. S. Tsai, R. G Bergman, J. A. Ellman, Acc. Chem. Res. 2011, 44, 814
22. c) F W. Patureau, J. Wencel-Delord, F Glorius, Aldrichimica Acta 2012, 45, 31
23. d) G Song, F Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
24. e) S. Chiba, Chem. Lett. 2012, 41, 1554
25. f) N. Kuhl, N. Schrçder, F. Glorius, Adv. Synth. Catal. 2014, 356, 1443.
26. a) F W Patureau, T. Besset, N. Kuhl, F Glorius, J. Am. Chem. Soc. 2011, 133, 2154
27. b) K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. Int. Ed. 2011, 50, 4169
28. Angew. Chem. 2011, 123, 4255
29. c) Z. Qi, M. Wang, X. Li, Org. Lett. 2013, 15, 5440
30. d) Y Chen, F Wang, W Zhen, X. Li, Adv. Synth. Catal. 2013, 355, 353
31. e) L. Dong, C.-H. Qu, J.-R. Huang, W Zhang, Q.-R. Zhang, J.-G Deng, Chem. Eur. J. 2013, 19, 16537
32. f) T Fukutani, N. Umeda, K. Hirano, T Satoh, M. Miura, Chem. Commun. 2009, 5141
33. g) B.-J. Li, H.-Y Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem. Int. Ed. 2012, 51, 3948
34. Angew. Chem. 2012, 124, 4014.
35. III-catalyzed directed C-H olefinations, see: a) K. Ueura, T Satoh, M. Miura, Org. Lett. 2007, 9, 1407
36. b) F W Patureau, F Glorius, J. Am. Chem. Soc. 2010, 132, 9982
37. c) F. Wang, G. Song, X. Li, Org. Lett. 2010, 12, 5430
38. d) F. W. Patureau, T. Besset, F Glorius, Angew. Chem. Int. Ed. 2011, 50, 1064
39. Angew. Chem. 2011, 123, 1096
40. e) T.-J. Gong, B. Xiao, Z.-J. Liu, J. Wan, J. Xu, D.-F Luo, Y. Fu, L. Liu, Org. Lett. 2011, 13, 3235
41. f) F W Patureau, C. Nimphius, F Glorius, Org. Lett. 2011, 13, 6346
42. g) A. S. Tsai, M. Brasse, R. G Bergman, J. A. Ellman, Org. Lett. 2011, 13, 540
43. h) S. H. Park, J. Y. Kim, S. Chang, Org. Lett. 2011, 13, 2372
44. i) C. Wang, H. Chen, Z. Wang, J. Chen, Y Huang, Angew. Chem. Int. Ed. 2012, 51, 7242
45. Angew. Chem. 2012, 124, 7354
46. j) W. Zhen, F Wang, W Zhao, Z. Du, X. Li, Angew. Chem. Int. Ed. 2012, 51, 11819
47. Angew. Chem. 2012, 124, 11989
48. k) J. Zhang, T.-P Loh, Chem. Commun. 2012, 48, 11232
49. l) L. Zheng, J. Wang, Chem. Eur. J. 2012, 18, 9699
50. m) Y Unoh, Y Hashimoto, D. Takeda, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2013, 15, 3258
51. n) M. Brasse, J. Cámpora, J. A. Ellman, R. G Bergman, J. Am. Chem. Soc. 2013, 135, 6427
52. o) B. Liu, Y Fan, Y Gao, C. Sun, C. Xu, J. Zhu, J. Am. Chem. Soc. 2013, 135, 468
53. p) X. Huang, J. Huang, C. Du, X. Zhang, F Song, J. You, Angew. Chem. Int. Ed. 2013, 52, 12970
54. Angew. Chem. 2013, 125, 13208.
55. a) F Kakiuchi, M. Matsumoto, K. Tsuchiya, K. Igi, T. Hayamizu, N. Chatani, S. Murai, J. Organomet. Chem. 2003, 686, 134
56. b) H.-J. Li, P.-H. Li, L. Wang, Org. Lett. 2013, 15, 620
57. c) K. Muralirajan, C.-H. Cheng, Chem. Eur. J. 2013, 19, 6198
58. d) D. Zhao, Q. Wu, X. Huang, F Song, T. Lv, J. You, Chem. Eur. J. 2013, 19, 6239
59. e) Y Lian, R. G Bergman, L. D. Lavis, J. A. Ellman, J. Am. Chem. Soc. 2013, 135, 7122.
60. a) T. Uemura, N. Chatani, J. Org. Chem. 2005, 70, 8631
61. b) K. Kisseljova, O. Tsubrik, R. Sillard, S. Mäeorg, U. Mäeorg, Org. Lett. 2006, 8, 43
62. c) O. Tsubrik, R. Sillard, U. Mäeorg, Synthesis 2006, 843.
63. CCDC1029702 (5a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
64. We presumed that the strong coordination of CHO to the [Rh] species probably is responsible for the favorable N - N bond cleavage.
65. N. J. Webb, S. P. Marsden, S. A. Raw, Org. Lett. 2014, 16, 4718.
66. a) J. T Klein, L. Davis, G E. Olsen, G S. Wong, F. P. Huger, C. P. Smith, W W Petko, M. Cornfeldt, J. C. Wilker, R. D. Blitzer, E. Landau, V. Harautunian, L. L. Martin, R. C. Effland, J. Med. Chem. 1996, 39, 570
67. b) T Itoh, M. Miyazaki, H. Maeta, Y Matsuya, K. Nagata, A. Ohsawa, Bioorg. Med. Chem. 2000, 8, 1983.
68. a) B. A. Frontana-Uribe, C. Moinet, L. Toupet, Eur. J. Org. Chem. 1999, 419
69. b) M. Watanabe, T Yamamoto, M. Nishiyama, Angew. Chem. Int. Ed. 2000, 39, 2501
70. Angew. Chem. 2000, 112, 2620
71. c) F Melkonyan, A. Topolyan, M. Yurovskaaya, A. Karchava, Eur. J. Org. Chem. 2008, 5952
72. d) N. Halland, M. Nazare, J. Alonso, O. R'kyek, A. Lindenschmidt, Chem. Commun. 2011, 47, 1042
73. e) E. Brachet, S. Messaoudi, J.-F Peyrat, J.-D. Brion, M. Alami, Adv. Synth. Catal. 2012, 354, 2829
74. f) Y Liang, K. Yu, B. Li, S. Xu, H. Song, B. Wang, Chem. Commun. 2014, 50, 6130.
75. Y Zhang, Q. Tang, M. Luo, Org. Biomol. Chem. 2011, 9, 4977.
76. M. Zhu, N. Zheng, Synthesis 2011, 2223.
77. a) M. Somei, K. Ura, Chem. Lett. 1978, 707
78. b) M. Somei, Y Kurizuka, Chem. Lett. 1979, 127.
79. a) K. Umemura, T. Mizushima, H. Katayama, Y Kiryu, T Yamori, T. Andoh, Mol. Pharmacol. 2002, 62, 873
80. b) Y.-M. Zhu, Y Kiryu, H. Katayama, Tetrahedron Lett. 2002, 43, 3577.
81. Here is a proposed reaction mechanism for the formation of 7a as a result of β-hydride elimination: (Equestion Presented)
82. a) W Jones, Acc. Chem. Res. 2003, 36, 140
83. b) E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066
84. Angew. Chem. 2012, 124, 3120.
85. L. Li, W W Brennessel, W. D. Jones, Organometallics 2009, 28, 3492.
86. D. L. Davies, O. Al-Duaij, J. Fawcett, M. Giardiello, S. T Hilton, D. R. Russell, Dalton Trans. 2003, 4132.
87. a) C. Wang, H. Sun, Y Fang, Y Huang, Angew. Chem. Int. Ed. 2013, 52, 5795
88. Angew. Chem. 2013, 125, 5907
89. b) D. Zhao, Z. Shi, F Glorius, Angew. Chem. Int. Ed. 2013, 52, 12426
90. Angew. Chem. 2013, 125, 12652.
91. a) S. Rakshit, C. Grohmann, T Besset, F Glorius, J. Am. Chem. Soc. 2011, 133, 2350
92. b) N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449
93. c) T K. Hyster, L. Knçrr, T. R. Ward, T. Rovis, Science 2012, 338, 500
94. d) B. Ye, N. Cramer, Science 2012, 338, 504
95. e) J. M. Neely, T Rovis, J. Am. Chem. Soc. 2013, 135, 66
96. f) D. Zhao, F Lied, F Glorius, Chem. Sci. 2014, 5, 2869.