Ruthenium-catalyzed regioselective C2 alkenylation of indoles and pyrroles via C-H bond functionalization

Journal of Organic Chemistry

Volumn 78, Issue 18, 2013, Pages 9345-9353

  Li, Bin ^a   Ma, Jianfeng ^a   Xie, Weijia ^a   Song, Haibin ^a   Xu, Shansheng ^a   Wang, Baiquan ^a,b  

^a NANKAI UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND FUNCTIONALIZATION; CATALYTIC REACTIONS; DIRECTING GROUPS; OXIDATIVE COUPLINGS; REGIO-SELECTIVE; STEREOSELECTIVE MANNER;

RUTHENIUM;

CATALYSIS;

ALKENE DERIVATIVE; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COVALENT BOND; ELECTROPHILICITY; NUCLEAR OVERHAUSER EFFECT; OXIDATIVE COUPLING; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 84884580258     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401579m     Document Type: Article

References (83)

1. Ackermann, L. Acc. Chem. Res. 2013, 10.1021/ar3002798
2. Kozhushkov, S. I.; Ackermann, L. Chem. Sci. 2013, 4, 886
3. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
4. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
5. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
6. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
7. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
8. Patureau, F. W.; Wencel-Delord, J.; Glorius, F. Aldrichimica Acta 2012, 45, 31
9. Engle, K. M.; Mei, T. S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
10. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
11. Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588
12. Bugaut, X.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 7479
13. Ackermann, L. Angew. Chem., Int. Ed. 2011, 50, 3842
14. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
15. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540
16. Hartwig, J. F. Chem. Soc. Rev. 2011, 40, 1992
17. Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912
18. Stokes, B. J.; Driver, T. G. Eur. J. Org. Chem. 2011, 4071
19. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
20. Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119
21. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
22. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
23. The Mizoroki-Heck Reaction; Oestreich, M., Ed.; Wiley: Chichester, 2009.
24. Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: New York, 2004; Chapter 5.
25. Li, D.-D.; Yuan, T.-T.; Wang, G.-W. Chem. Commun. 2011, 47, 12789
26. Lu, Y.; Leow, D.; Wang, X.; Engel, K. M.; Yu, J.-Q. Chem. Sci. 2011, 2, 967
27. Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
28. Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460
29. Lu, Y.; Wang, D.-H.; Engle, K.-M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916
30. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680
31. Nishikata, T.; Lipshutz, B. H. Org. Lett. 2010, 12, 1972 and references cited therein
32. Zhu, C.; Flack, J. R. Chem. Commun. 2012, 48, 1674
33. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
34. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064
35. Besset, T.; Kuhl, N.; Patureau, F. W.; Glorius, F. Chem.-Eur. J. 2011, 17, 7167
36. Tsai, A. S.; Brasse, M.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2011, 13, 540
37. Park, S.; Kim, J. Y.; Chang, S. Org. Lett. 2011, 13, 2372
38. Feng, C.; Loh, T.-P. Chem. Commun. 2011, 47, 10458
39. Gong, T.-J.; Xiao, B.; Liu, Z.-J.; Wan, J.; Xu, J.; Luo, D.-F.; Fu, Y.; Liu, L. Org. Lett. 2011, 13, 3235
40. Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 3024
41. Wang, F.; Song, G.; Du, Z.; Li, X. J. Org. Chem. 2011, 76, 2926
42. Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982
43. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
44. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
45. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
46. Thomson, R. H. The Chemistry of Natural Products; Blackie and Son: Glasgow, 1985.
47. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045
48. Garg, N. K.; Sarpong, R.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 13179
49. Tois, J.; Franzén, R.; Koskinen, A. Tetrahedron 2003, 59, 5395
50. Chen, F.-E.; Huang, J. Chem. Rev. 2005, 105, 4671
51. García-Rubia, A.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48, 6515
52. García-Rubia, A.; Arrayás, R. G.; Carretero, J. C. Chem.-Eur. J. 2010, 16, 9676
53. Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159
54. Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125
55. Capito, E.; Brown, J. M.; Ricci, A. Chem. Commun. 2005, 1854
56. Ueyama, T.; Mochida, S.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 706
57. Hashimoto, Y.; Ortloff, T.; Hirano, K.; Satoh, T.; Bolm, C.; Miura, M. Chem. Lett. 2012, 41, 151
58. Ackermann, L.; Pospech, J. Org. Lett. 2011, 13, 4153
59. Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728
60. Graczyk, K.; Ma, W.; Ackermann, L. Org. Lett. 2012, 14, 4110
61. Li, J.; Kornhaaß, C.; Ackermann, L. Chem. Commun. 2012, 48, 11343
62. Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Green Chem. 2011, 13, 3075
63. Singh, K. S.; Dixneuf, P. H. Organometallics 2012, 31, 7320
64. Padala, K.; Jeganmohan, M. Org. Lett. 2011, 13, 6144
65. Padala, K.; Jeganmohan, M. Org. Lett. 2012, 14, 1134
66. Chidipudi, S. R.; Wieczysty, M. D.; Khan, I.; Lam, H. W. Org. Lett. 2013, 15, 570
67. Goriya, Y.; Ramana, C. V. Chem.-Eur. J. 2012, 18, 13288
68. Li, B.; Ma, J.; Liang, Y.; Wang, N.; Xu, S.; Song, H.; Wang, B. Eur. J. Org. Chem. 2013, 1950
69. Li, B.; Ma, J.; Wang, N.; Feng, H.; Xu, S.; Wang, B. Org. Lett. 2012, 14, 736
70. Li, B.; Feng, H.; Xu, S.; Wang, B. Chem.-Eur. J. 2011, 17, 12573
71. Lanke, V.; Prabhu, K. Org. Lett. 2013, 15, 2818
72. Li, B.; Ma, J.; Xie, W.; Song, H.; Xu, S.; Wang, B. Chem.-Eur. J. 2013, 19, 11863
73. Schipper, D. J.; Hutchinson, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6910
74. Zhou, B.; Yang, Y.; Li, Y. Chem. Commun. 2012, 48, 5163 and also see ref 19b.
75. Wang, H.; Schröder, N.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 5386
76. Li, X.; Gong, X.; Zhao, M.; Song, G.; Deng, J.; Li, X. Org. Lett. 2011, 13, 5808
77. It is possible that the allyl substrate affords product by a different mechanism; see: Zaitsev, A. B.; Gruber, S.; Plüss, P. A.; Pregosin, P. S.; Veiros, L. F.; Wörle, M. J. Am. Chem. Soc. 2008, 130, 11604
78. For an excellent report on the Pd(II)-catalyzed diastereoselective C-2 alkenylation of indoles, see: Kandukuri, S. R.; Schiffner, J. A.; Oestreich, M. Angew. Chem., Int. Ed. 2012, 51, 1265
79. At present, we do not know the exact reason why cyclopent-2-enone gave the addition product. Lee et al. recently reported that more polar solvents promote the oxidative Heck reaction over conjugate addition on cyclic Michael acceptor substrates; see: Walker, S. E.; Boehnke, J.; Glen, P. E.; Levey, S.; Patrick, L.; Jordan-Hore, J. A.; Lee, A.-L. Org. Lett. 2013, 15, 1886
80. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233
81. Hibino, S.; Sugino, E.; Kuwada, T.; Ogura, N.; Sato, K.; Choshi, T. J. Org. Chem. 1992, 57, 5917
82. Sheldrick, G. M. Program for Empirical Absorption Correction of Area Detector data; University of Göttingen: Göttingen, Germany, 1996.
83. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures from Diffraction Data; University of Göttingen: Göttingen, Germany, 1997.