Cobalt(II) Porphyrin-Catalyzed Intramolecular Cyclopropanation of N-Alkyl Indoles/Pyrroles with Alkylcarbene: Efficient Synthesis of Polycyclic N-Heterocycles

Angewandte Chemie - International Edition

Volumn 55, Issue 5, 2016, Pages 1810-1815

  Reddy, Annapureddy Rajasekar ^a,b   Hao, Fei ^a,b   Wu, Kai ^a,b   Zhou, Cong Ying ^a,b   Che, Chi Ming ^a,b  

^a UNIVERSITY OF HONG KONG   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

carbenes; cobalt; fused ring systems; heterocycles; porphyrinoids

Indexed keywords

CATALYSIS; NITROGEN; ORGANIC COMPOUNDS; PORPHYRINS;

CARBENES; EFFICIENT SYNTHESIS; FUSED-RING SYSTEM; HETEROCYCLES; INTRAMOLECULAR CYCLOPROPANATIONS; POLYCYCLIC COMPOUNDS; PORPHYRINOIDS; REACTION CONDITIONS;

COBALT;

EID: 84955705270     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201506418     Document Type: Article

References (87)

1. X. Xu, M. P. Doyle, Acc. Chem. Res. 2014, 47, 1396;
2. H. M. L. Davies, J. E. Spangler, Adv. Heterocycl. Chem. 2013, 110, 43 (Ed.: A. Katritzky), Elsevier Inc
3. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704;
4. H. M. L. Davies, S. J. Hedley, Chem. Soc. Rev. 2007, 36, 1109.
5. Y. Xia, Y. Zhang, J. Wang, ACS Catal. 2013, 3, 2586;
6. Q. Xiao, Y. Zhang, J. Wang, Acc. Chem. Res. 2013, 46, 236;
7. Z. Shao, H. Zhang, Chem. Soc. Rev. 2012, 41, 560;
8. Y. Zhang, J. Wang, Eur. J. Org. Chem. 2011, 1015;
9. J. Barluenga, C. Valdés, Angew. Chem. Int. Ed. 2011, 50, 7486;
10. Angew. Chem. 2011, 123, 7626;
11. J. R. Fulton, V. K. Aggarwal, J. de Vicente, Eur. J. Org. Chem. 2005, 1479.
12. B. Morandi, E. M. Carreira, Science 2012, 335, 1471;
13. J. Barluenga, N. Quiñones, M. Tomás-Gamasa, M.-P. Cabal, Eur. J. Org. Chem. 2012, 2312;
14. J.-L. Zhang, P. W. H. Chan, C.-M. Che, Tetrahedron Lett. 2003, 44, 8733;
15. V. K. Aggarwal, J. de Vicente, R. V. Bonnert, Org. Lett. 2001, 3, 2785.
16. A. R. Reddy, C.-Y. Zhou, Z. Guo, J. Wei, C.-M. Che, Angew. Chem. Int. Ed. 2014, 53, 14175;
17. Angew. Chem. 2014, 126, 14399.
18. H. Hussain, A. Al-Harrasi, A. Al-Rawahi, I. R. Green, S. Gibbons, Chem. Rev. 2014, 114, 10369;
19. E. Vitaku, D. T. Smith, J. T. Njardarson, J. Med. Chem. 2014, 57, 10257;
20. V. Sridharan, P. A. Suryavanshi, J. C. Menéndez, Chem. Rev. 2011, 111, 7157;
21. J.-F. Hu, H. Fan, J. Xiong, S.-B. Wu, Chem. Rev. 2011, 111, 5465;
22. R. A. Pilli, G. B. Rosso, M. C. F. de Oliveira, Nat. Prod. Rep. 2010, 27, 1908;
23. S. R. Walker, E. J. Carter, B. C. Huff, J. C. Morris, Chem. Rev. 2009, 109, 3080;
24. A. Kornienko, A. Evidente, Chem. Rev. 2008, 108, 1982;
25. H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev. 2008, 108, 264.
26. M. Nettekoven, J.-M. Plancher, H. Richter, O. Roche, S. Taylor, PCT Int. Appl. WO US 2007/0135416 A1, 2007;
27. S. Jolidon, R. Narquizian, R. D. Norcross, E. Pinard, PCT Int. Appl. WO US 2006/0128712 A1, 2006;
28. P. Hebeisen, P. Mattei, M. Muller, H. Richter, S. Roever, S. Taylor, PCT Int. Appl. WO 02/072584 A2, 2002;
29. R. M. Shaheen, D. W. Davis, W. Liu, B. K. Zebrowski, M. R. Wilson, C. D. Bucana, D. J. McConkey, G. McMahon, L. M. Ellis, Cancer Res. 1999, 59, 5412;
30. T. F. Molinski, Chem. Rev. 1993, 93, 1825.
31. A. D. Yamaguchi, K. M. Chepiga, J. Yamaguchi, K. Itami, H. M. L. Davies, J. Am. Chem. Soc. 2015, 137, 644;
32. X. Gao, B. Wu, W.-X. Huang, M.-W. Chen, Y.-G. Zhou, Angew. Chem. Int. Ed. 2015, 54, 11956;
33. Angew. Chem. 2015, 127, 12124;
34. J.-M. Yang, C.-Z. Zhu, X.-Y. Tang, M. Shi, Angew. Chem. Int. Ed. 2014, 53, 5142;
35. Angew. Chem. 2014, 126, 5242;
36. A. DeAngelis, V. W. Shurtleff, O. Dmitrenko, J. M. Fox, J. Am. Chem. Soc. 2011, 133, 1650;
37. Y. Cai, S.-F. Zhu, G.-P. Wang, Q.-L. Zhou, Adv. Synth. Catal. 2011, 353, 2939;
38. T. Goto, Y. Natori, K. Takeda, H. Nambu, S. Hashimoto, Tetrahedron: Asymmetry 2011, 22, 907. Selected examples for cyclopropanation:
39. G. Özüduru, T. Schubach, M. M. K. Boysen, Org. Lett. 2012, 14, 4990;
40. D. Gagnon, C. Spino, J. Org. Chem. 2009, 74, 6035;
41. S. J. Hedley, D. L. Ventura, P. M. Dominiak, C. L. Nygren, H. M. L. Davies, J. Org. Chem. 2006, 71, 5349;
42. F. Gnad, M. Poleschak, O. Reiser, Tetrahedron Lett. 2004, 45, 4277.
43. C.-Y. Zhou, V. K.-Y. Lo, C.-M. Che, Handbook of Porphyrin Science, Vol. 21 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific, Singapore, 2012, p. 321;
44. G. Simonneaux, P. Le Maux, S. Chevance, H. Srour, Handbook of Porphyrin Science, Vol. 21 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific, Singapore, 2012, p. 377;
45. D. Intrieri, A. Caselli, E. Gallo, Eur. J. Inorg. Chem. 2011, 5071;
46. C.-M. Che, V. K.-Y. Lo, C.-Y. Zhou, J.-S. Huang, Chem. Soc. Rev. 2011, 40, 1950;
47. H. Lu, X. P. Zhang, Chem. Soc. Rev. 2011, 40, 1899;
48. J. V. Ruppel, K. B. Fields, N. L. Snyder, X. P. Zhang, Handbook of Porphyrin Science, Vol. 10 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific, Singapore, 2010, p. 1.
49. X. Cui, X. Xu, L.-M. Jin, L. Wojtas, X. P. Zhang, Chem. Sci. 2015, 6, 1219;
50. X. Xu, H. Lu, J. V. Ruppel, X. Cui, S. L. de Mesa, L. Wojtas, X. P. Zhang, J. Am. Chem. Soc. 2011, 133, 15292;
51. W. I. Dzik, X. Xu, X. P. Zhang, J. N. H. Reek, B. de Bruin, J. Am. Chem. Soc. 2010, 132, 10891;
52. Y. Chen, J. V. Ruppel, X. P. Zhang, J. Am. Chem. Soc. 2007, 129, 12074. Ru:
53. A. R. Reddy, C.-Y. Zhou, C.-M. Che, Org. Lett. 2014, 16, 1048;
54. C.-M. Ho, J.-L. Zhang, C.-Y. Zhou, O.-Y. Chan, J. J. Yan, F.-Y. Zhang, J.-S. Huang, C.-M. Che, J. Am. Chem. Soc. 2010, 132, 1886. Ir:
55. J.-C. Wang, Y. Zhang, Z.-J. Xu, V. K.-Y. Lo, C.-M. Che, ACS Catal. 2013, 3, 1144;
56. J.-C. Wang, Z.-J. Xu, Z. Guo, Q.-H. Deng, C.-Y. Zhou, X.-L. Wan, C.-M. Che, Chem. Commun. 2012, 48, 4299;
57. B. J. Anding, A. Ellern, L. K. Woo, Organometallics 2012, 31, 3628. Rh:
58. H.-Y. Thu, G. S.-M. Tong, J.-S. Huang, S. L.-F. Chan, Q.-H. Deng, C.-M. Che, Angew. Chem. Int. Ed. 2008, 47, 9747;
59. Angew. Chem. 2008, 120, 9893. Fe:
60. G.-Q. Chen, Z.-J. Xu, C.-Y. Zhou, C.-M. Che, Chem. Commun. 2011, 47, 10963;
61. H. M. Mbuvi, L. K. Woo, Organometallics 2008, 27, 637.
62. T.-S. Kam, K.-H. Lim, K. Yoganathan, M. Hayashi, K. Komiyama, Tetrahedron 2004, 60, 10739;
63. T.-S. Kam, K. Yoganathan, C.-H. Chuah, Tetrahedron Lett. 1995, 36, 759;
64. W. J. Welstead, H. F. Stauffer, L. F. Sancilio, J. Med. Chem. 1974, 17, 544;
65. D. Zhang, H. Song, Y. Qin, Acc. Chem. Res. 2011, 44, 447.
66. C. Beemelmanns, V. Blot, S. Gross, D. Lentz, H.-U. Reissig, Eur. J. Org. Chem. 2010, 2716;
67. J. B. Hester, Jr., B. N. Rogers, E. J. Jacobsen, M. D. Ennis, B. A. Acker, S. L. Vander Velde, PCT Int. Appl. 2000, WO 2000064899 A1 20001102.
68. CCDC 1412061 (2 d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
69. C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 2004, 126, 15378.
70. C. C. Dudman, C. B. Reese, Synthesis 1982, 419.
71. J. A. Edgar, R. J. Molyneux, S. M. Colegate, Chem. Res. Toxicol. 2015, 28, 4;
72. J. Robertson, K. Stevens, Nat. Prod. Rep. 2014, 31, 1721;
73. J. P. Michael, Nat. Prod. Rep. 2005, 22, 603;
74. Y. Cheng, Z. T. Huang, M. X. Wang, Curr. Org. Chem. 2004, 8, 325.
75. M. M. Fashe, R. O. Juvonen, A. Petsalo, M. Rahnasto-Rilla, S. Auriola, P. Soininen, J. Vepsalainen, M. Pasanen, Chem. Res. Toxicol. 2014, 27, 1950;
76. P. Sonnet, P. Dallemagne, J. Guillon, C. Enguehard, S. Stiebing, J. Tanguy, R. Bureau, S. Rault, P. Auvray, S. Moslemi, P. Sourdaine, G. E. Seralini, Bioorg. Med. Chem. 2000, 8, 945;
77. F. Schröder, V. Sinnwell, H. Baumann, M. Kaib, W. Francke, Angew. Chem. Int. Ed. Engl. 1997, 36, 77;
78. Angew. Chem. 1997, 109, 161;
79. A. Gusman, F. Yuste, R. A. Toscano, J. M. Young, A. R. Van Horn, J. M. Muchowski, J. Med. Chem. 1986, 29, 589.
80. S. Maity, M. Zhu, R. S. Shinabery, N. Zheng, Angew. Chem. Int. Ed. 2012, 51, 222;
81. Angew. Chem. 2012, 124, 226.
82. L. S. Fernandez, M. S. Buchanan, A. R. Carroll, Y. J. Feng, R. J. Quinn, V. M. Avery, Org. Lett. 2009, 11, 329;
83. P. E. Mahaney, A. T. Vu, C. C. McComas, P. Zhang, L. M. Nogle, W. L. Watts, A. Sarkahian, L. Leventhal, N. R. Sullivan, A. J. Uveges, E. J. Trybulski, Bioorg. Med. Chem. 2006, 14, 8455;
84. D. Paris, M. Cottin, P. Demonchaux, G. Augert, P. Dupassieux, P. Lenoir, M. J. Peck, D. Jasserand, J. Med. Chem. 1995, 38, 669; for a review:
85. U. Galm, M. H. Hager, S. G. Van Lanen, J. Ju, J. S. Thorson, B. Shen, Chem. Rev. 2005, 105, 739.
86. J. Yin, T. Linker, Org. Biomol. Chem. 2012, 10, 2351;
87. P. Bertinato, E. J. Sorensen, D. Meng, S. J. Danishefsky, J. Org. Chem. 1996, 61, 8000.