Rhodium-Catalyzed Tandem Annulation Reactions of 7-Azaindoles with Electron-Deficient Olefins via Double CH Activation

Advanced Synthesis and Catalysis

Volumn 358, Issue 10, 2016, Pages 1595-1601

  Li, Shuai Shuai ^a,b,c   Lin, Hui ^a   Liu, Chen Fei ^a   Xia, Ying Qi ^a   Zhang, Xiao Mei ^b   Dong, Lin ^a  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

7 azaindoles; C Michael cyclization; C H activation; electron deficient alkenes; rhodium

Indexed keywords

EID: 84964714027     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201600112     Document Type: Article

References (71)

1. J. J. Song, J. T. Reeves, F. Gallou, Z. Tan, N. K. Yee, C. H. Senanayake, Chem. Soc. Rev. 2007, 36, 1120–1132;
2. D. Song, H. Schmider, S. Wang, Org. Lett. 2002, 4, 4049–4052;
3. F. Popowycz, S. Routier, B. Joseph, J.-Y. Mérour, Tetrahedron 2007, 63, 1031–1064;
4. H. L. Milton, M. V. Wheatley, A. M. Slawin, J. D. Woollins, Inorg. Chem. Commun. 2004, 7, 1106–1108;
5. J.-Y. Mérour, S. Routier, F. Suzenet, B. Joseph, Tetrahedron 2013, 69, 4767–4834;
6. Q. Wu, J. A. Lavigne, Y. Tao, M. D′Iorio, S. Wang, Chem. Mater. 2001, 13, 71–77;
7. A. Echalier, K. Bettayeb, Y. Ferandin, O. Lozach, M. Clément, A. Valette, F. Liger, B. Marquet, J. C. Morris, J. A. Endicott, J. Med. Chem. 2008, 51, 737–751;
8. Q. Wu, A. Hook, S. Wang, Angew. Chem. 2000, 112, 4094–4096;
9. Angew. Chem. Int. Ed. 2000, 39, 3933–3935;
10. Y.-S. Tung, M. S. Coumar, Y.-S. Wu, H.-Y. Shiao, J.-Y. Chang, J.-P. Liou, P. Shukla, C.-W. Chang, C.-Y. Chang, C.-C. Kuo, J. Med. Chem. 2011, 54, 3076–3080;
11. N. M. Barl, E. Sansiaume-Dagousset, K. Karaghiosoff, P. Knochel, Angew. Chem. 2013, 125, 10278–10281;
12. Angew. Chem. Int. Ed. 2013, 52, 10093–10096.
13. L. C. Cooper, G. G. Chicchi, K. Dinnell, J. M. Elliott, G. J. Hollingworth, M. M. Kurtz, K. L. Locker, D. Morrison, D. E. Shaw, K.-L. Tsao, Bioorg. Med. Chem. Lett. 2001, 11, 1233–1236.
14. A. Mullard, Nat. Rev. Drug Discovery 2012, 11, 91–94.
15. A. Zambon, I. Niculescu-Duvaz, D. Niculescu-Duvaz, R. Marais, C. J. Springer, Bioorg. Med. Chem. Lett. 2012, 22, 789–792.
16. Y. Chen, S. Guo, K. Li, J. Qu, H. Yuan, Q. Hua, B. Chen, Adv. Synth. Catal. 2013, 355, 711–715;
17. P. Kannaboina, K. Anilkumar, S. Aravinda, R. A. Vishwakarma, P. Das, Org. Lett. 2013, 15, 5718–5721;
18. M. P. Huestis, K. Fagnou, Org. Lett. 2009, 11, 1357–1360.
19. G. Qian, X. Hong, B. Liu, H. Mao, B. Xu, Org. Lett. 2014, 16, 5294–5297;
20. S.-S. Li, C.-Q. Wang, H. Lin, X.-M. Zhang, L. Dong, Org. Lett. 2015, 17, 3018–3021;
21. S.-S. Li, C.-Q. Wang, H. Lin, X.-M. Zhang, L. Dong, Org. Biomol. Chem. 2016, 14, 229–237.
22. P. Nuhant, C. Allais, M.-Z. Chen, J. W. Coe, A. Dermenci, O. O. Fadeyi, A. C. Flick, J. J. Mousseau, Org. Lett. 2015, 17, 4292–4295;
23. A. Plas, C. Martin, N. Joubert, M.-C. Viaud-Massuard, Org. Lett. 2015, 17, 4710–4713.
24. S. Luo, F.-X. Luo, X.-S. Zhang, Z.-J. Shi, Angew. Chem. 2013, 125, 10792–10795;
25. Angew. Chem. Int. Ed. 2013, 52, 10598–10601;
26. C. Suzuki, K. Morimoto, K. Hirano, T. Satoh, M. Miura, Adv. Synth. Catal. 2014, 356, 1521–1526;
27. H. Gong, H. Zeng, F. Zhou, C.-J. Li, Angew. Chem. 2015, 127, 5810–5813;
28. Angew. Chem. Int. Ed. 2015, 54, 5718–5721;
29. L. Wan, N. Dastbaravardeh, G. Li, J.-Q. Yu, J. Am. Chem. Soc. 2013, 135, 18056–18059;
30. S. Nakanowatari, L. Ackermann, Chem. Eur. J. 2014, 20, 5409–5413;
31. J. Chen, K. Natte, A. Spannenberg, H. Neumann, M. Beller, X.-F. Wu, Chem. Eur. J. 2014, 20, 14189–14193;
32. H. Lee, Y. K. Sim, J. W. Park, C. H. Jun, Chem. Eur. J. 2014, 20, 323–333;
33. J.-Y. Mo, L.-H. Wang, X.-L. Cui, Org. Lett. 2015, 17, 4960–4963.
34. F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982–9983;
35. D. Wang, F. Wang, G. Song, X. Li, Angew. Chem. 2012, 124, 12514–12518;
36. Angew. Chem. Int. Ed. 2012, 51, 12348–12352;
37. H. Wang, N. Schroeder, F. Glorius, Angew. Chem. 2013, 125, 5495–5499;
38. Angew. Chem. Int. Ed. 2013, 52, 5386–5389;
39. H. Wang, B. Beiring, D. G. Yu, K. D. Collins, F. Glorius, Angew. Chem. 2013, 125, 12657–12661;
40. Angew. Chem. Int. Ed. 2013, 52, 12430–12434;
41. A. S. Tsai, M. Brasse, R. G. Bergman, J. A. Ellman, Org. Lett. 2010, 13, 540–542;
42. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212–11222;
43. X.-S. Zhang, Y.-F. Zhang, Z.-W. Li, F.-X. Luo, Z.-J. Shi, Angew. Chem. 2015, 127, 5568–5572;
44. Angew. Chem. Int. Ed. 2015, 54, 5478–5482;
45. X.-Z. Shu, C. M. Schienebeck, X.-X. Li, X. Zhou, W.-Z. Song, L.-Q. Chen, I. A. Guzei, W.-P. Tang, Org. Lett. 2015, 17, 5032–5035.
46. T.-J. Gong, B. Xiao, Z.-J. Liu, J. Wan, J. Xu, D.-F. Luo, Y. Fu, L. Liu, Org. Lett. 2011, 13, 3235–3237;
47. M. Zhang, H.-J. Zhang, T. Han, W. Ruan, T.-B. Wen, J. Org. Chem. 2015, 80, 620–627;
48. C. Feng, D.-M. Feng, T.-P. Loh, Org. Lett. 2013, 15, 3670–3673;
49. A. S. Tsai, M. B. Brasse, R. G. Bergman, J. A. Ellman, Org. Lett. 2011, 13, 540–542;
50. F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096–1099;
51. Angew. Chem. Int. Ed. 2011, 50, 1064–1067.
52. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407–1409;
53. J. Chen, G.-Y. Song, C.-L. Pan, X. Li, Org. Lett. 2010, 12, 5426–5429;
54. X.-T. Li, X. Gong, M. Zhao, G.-Y. Song, J. Deng, X. Li, Org. Lett. 2011, 13, 5808–5811;
55. G. Li, Z. Ding, B. Xu, Org. Lett. 2012, 14, 5338–5341.
56. For selected Rh-catalyzed intramolecular direct CC coupling reactions, see:
57. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624–655;
58. M. M. Coulter, P. K. Dornan, V. M. Dong, J. Am. Chem. Soc. 2009, 131, 6932–6933;
59. T. A. Davis, T. K. Hyster, T. Rovis, Angew. Chem. 2013, 125, 14431–14435;
60. Angew. Chem. Int. Ed. 2013, 52, 14181–14185;
61. B. Ye, P. A. Donets, N. Cramer, Angew. Chem. 2014, 126, 517–521;
62. Angew. Chem. Int. Ed. 2014, 53, 507–511.
63. L. A. Crawford, H. McNab, A. R. Mount, J. Verhille, S. I. Wharton, Synthesis 2010, 923–928.
64. For more details see the Supporting Information.
65. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651–3678;
66. F. W. Patureau, J. W. Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31–41;
67. J. A. Boerth, J. A. Ellman, Chem. Sci. 2016, 7, 1474–1479.
68. S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 10848–10849;
69. S. I. Gorelsky, Organometallics 2012, 31, 794–797;
70. S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Org. Chem. 2012, 77, 658–668;
71. L. Ackermann, Chem. Rev. 2011, 111, 1315–1345.