Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage

Angewandte Chemie - International Edition

Volumn 55, Issue 9, 2016, Pages 3208-3211

  Lerchen, Andreas ^a   Vásquez Céspedes, Suhelen ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

C H activation; CoIII catalysis; Cp; indoles; N N bond cleavage; redox neutral

Indexed keywords

ACTIVATION ANALYSIS; COBALT;

BOND CLEAVAGES; C-H ACTIVATION; DIRECT SYNTHESIS; DIRECTING GROUPS; INDOLES; REDOX-NEUTRAL; SYNTHETIC APPROACH;

CATALYSIS;

EID: 84959516519     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201510705     Document Type: Article

References (119)

1. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624;
2. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212;
3. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879;
4. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31;
5. N. Kuhl, N. Schröder, F. Glorius, Adv. Synth. Catal. 2014, 356, 1443;
6. D. Zhao, J. You, C. Hu, Chem. Eur. J. 2011, 17, 5466;
7. L. Ackermann, Chem. Rev. 2011, 111, 1315;
8. L. Ackermann, Acc. Chem. Res. 2014, 47, 281;
9. G. Song, X. Li, Acc. Chem. Res. 2015, 48, 1007;
10. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654;
11. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885;
12. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788;
13. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780;
14. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068;
15. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960;
16. Angew. Chem. 2012, 124, 9092;
17. S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. Int. Ed. 2014, 53, 74;
18. Angew. Chem. 2014, 126, 76;
19. X.-S. Zhang, K. Chen, Z.-J. Shi, Chem. Sci. 2014, 5, 2146.
20. A. A. Kulkarni, O. Daugulis, Synthesis 2009, 4087;
21. K. Gao, N. Yoshikai, Acc. Chem. Res. 2014, 47, 1208;
22. L. Ackermann, J. Org. Chem. 2014, 79, 8948;
23. I. Bauer, H.-J. Knölker, Chem. Rev. 2015, 115, 3170;
24. S. Z. Tasker, E. A. Standley, T. F. Jamison, Nature 2014, 509, 299;
25. J. J. Mousseau, A. B. Charette, Acc. Chem. Res. 2013, 46, 412.
26. T. Yoshino, H. Ikemoto, S. Matsunaga, M. Kanai, Angew. Chem. Int. Ed. 2013, 52, 2207;
27. Angew. Chem. 2013, 125, 2263;
28. T. Yoshino, H. Ikemotu, S. Matsunaga, M. Kanai, Chem. Eur. J. 2013, 19, 9142;
29. H. Ikemoto, T. Yoshino, K. Sakata, S. Matsunaga, M. Kanai, J. Am. Chem. Soc. 2014, 136, 5424;
30. B. Sun, T. Yoshino, S. Matsunaga, M. Kanai, Adv. Synth. Catal. 2014, 356, 1491;
31. B. Sun, T. Yoshino, S. Matsunaga, M. Kanai, Chem. Commun. 2015, 51, 4659;
32. Y. Suzuki, B. Sun, T. Yoshino, M. Kanai, S. Matsunaga, Tetrahedron 2015, 71, 4552;
33. Y. Suzuki, B. Sun, K. Sakata, S. Matsunaga, M. Kanai, Angew. Chem. Int. Ed. 2015, 54, 9944;
34. Angew. Chem. 2015, 127, 10082.
35. J. R. Hummel, J. A. Ellman, J. Am. Chem. Soc. 2015, 137, 490;
36. J. R. Hummel, J. A. Ellman, Org. Lett. 2015, 17, 2400.
37. T. M. Figg, S. Park, J. Park, S. Chang, D. G. Musaev, Organometallics 2014, 33, 4076;
38. P. Patel, S. Chang, ACS Catal. 2015, 5, 853;
39. A. B. Pawar, S. Chang, Org. Lett. 2015, 17, 660;
40. J. Park, S. Chang, Angew. Chem. Int. Ed. 2015, 54, 14103;
41. Angew. Chem. 2015, 127, 14309.
42. J. Li, L. Ackermann, Angew. Chem. Int. Ed. 2015, 54, 3635;
43. Angew. Chem. 2015, 127, 3706;
44. J. Li, L. Ackermann, Angew. Chem. Int. Ed. 2015, 54, 8551;
45. Angew. Chem. 2015, 127, 8671;
46. M. Moselage, N. Sauermann, J. Koeller, W. Liu, D. Gelman, L. Ackermann, Synlett 2015, 1596;
47. N. Sauermann, M. J. González, L. Ackermann, Org. Lett. 2015, 17, 5316.
48. D.-G. Yu, T. Gensch, F. de Azambuja, S. Vásquez-Céspedes, F. Glorius, J. Am. Chem. Soc. 2014, 136, 17722;
49. D. Zhao, J. H. Kim, L. Stegemann, C. A. Strassert, F. Glorius, Angew. Chem. Int. Ed. 2015, 54, 4508;
50. Angew. Chem. 2015, 127, 4591;
51. T. Gensch, S. Vásquez-Céspedes, D.-G. Yu, F. Glorius, Org. Lett. 2015, 17, 3714.
52. X.-G. Liu, S.-S. Zhang, C.-Y. Jiang, J.-Q. Wu, Q. Li, H. Wang, Org. Lett. 2015, 17, 5404;
53. X. Liu, S. Zhang, J. Wu, Q. Li, H. Wang, Tetrahedron Lett. 2015, 56, 4093;
54. N. Yoshikai, ChemCatChem 2015, 7, 732;
55. Y. Liang, Y.-F. Liang, C. Tang, Y. Yuan, N. Jiao, Chem. Eur. J. 2015, 21, 16395;
56. E. Ozkal, B. Cacherat, B. Morandi, ACS Catal. 2015, 5, 6458;
57. Z.-Z. Zhang, B. Liu, C.-Y. Wang, B.-F. Shi, Org. Lett. 2015, 17, 4094.
58. M. Zhang, Y. Zhang, X. Jie, H. Zhao, G. Li, W. Su, Org. Chem. Front. 2014, 1, 843;
59. Z. Chen, B. Wang, J. Zhang, W. Yu, Z. Liu, Y. Zhang, Org. Chem. Front. 2015, 2, 1107; for oxidizing directing groups:
60. J. Mo, L. Wang, Y. Liu, X. Cui, Synthesis 2015, 439;
61. H. Huang, X. Ji, W. Wu, H. Jiang, Chem. Soc. Rev. 2015, 44, 1155.
62. B. Sun, T. Yoshino, M. Kanai, S. Matsunaga, Angew. Chem. Int. Ed. 2015, 54, 12968;
63. Angew. Chem. 2015, 127, 13160;
64. H. Wang, J. Koeller, W. Liu, L. Ackermann, Chem. Eur. J. 2015, 21, 15525;
65. M. Sen, D. Kalsi, B. Sundararaju, Chem. Eur. J. 2015, 21, 15529.
66. R. J. Sundberg, Indoles, Academic Press, San Diego, 1996;
67. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles: Structure, Reactions, Syntheses and Applications, 2 nd ed., Wiley-VCH, Weinheim, 2003;
68. M. Somei, F. Yamada, Nat. Prod. Rep. 2004, 21, 278;
69. M. Somei, F. Yamada, Nat. Prod. Rep. 2005, 22, 73;
70. A. J. Kochanowska-Karamyan, M. T. Hamann, Chem. Rev. 2010, 110, 4489;
71. T. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761.
72. M. Inman, C. J. Moody, Chem. Sci. 2013, 4, 29;
73. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875;
74. S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873;
75. S. Cacchi, G. Fabrizi, Chem. Rev. 2011, 111, PR 215;
76. M. Shiri, Chem. Rev. 2012, 112, 3508;
77. K. Krüger (née Alex), A. Tillack, M. Beller, Adv. Synth. Catal. 2008, 350, 2153;
78. N. Yoshikai, Y. Wei, Asian J. Org. Chem. 2013, 2, 466.
79. S. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, F. Glorius, Angew. Chem. Int. Ed. 2008, 47, 7230;
80. Angew. Chem. 2008, 120, 7340;
81. J. J. Neumann, S. Rakshit, T. Dröge, F. Glorius, Chem. Eur. J. 2011, 17, 7298;
82. Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y. Cui, N. Jiao, Angew. Chem. Int. Ed. 2009, 48, 4572;
83. Angew. Chem. 2009, 121, 4642;
84. Y. Wei, I. Deb, N. Yoshikai, J. Am. Chem. Soc. 2012, 134, 9098;
85. J. Chen, Q. Pang, Y. Sun, X. Li, J. Org. Chem. 2011, 76, 3523; rhodium:
86. D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474;
87. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326;
88. C. Wang, H. Sun, Y. Fang, Y. Huang, Angew. Chem. Int. Ed. 2013, 52, 5795;
89. Angew. Chem. 2013, 125, 5907; ruthenium:
90. L. Ackermann, A. V. Lygin, Org. Lett. 2012, 14, 764.
91. J. Wu, X. Cui, L. Chen, G. Jiang, Y. Wu, J. Am. Chem. Soc. 2009, 131, 13888;
92. Y. Tan, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 3676; rhodium:
93. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350;
94. H. Wang, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 7318;
95. Angew. Chem. 2012, 124, 7430;
96. H. Wang, C. Grohmann, C. Nimphius, F. Glorius, J. Am. Chem. Soc. 2012, 134, 19592;
97. N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6908;
98. N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449;
99. P. C. Too, Y.-F. Wang, S. Chiba, Org. Lett. 2010, 12, 5688;
100. X. Zhang, D. Chen, M. Zhao, J. Zhao, A. Jia, X. Li, Adv. Synth. Catal. 2011, 353, 719;
101. T. K. Hyster, K. E. Ruhl, T. Rovis, J. Am. Chem. Soc. 2013, 135, 5364;
102. X. Xu, Y. Liu, C.-M. Park, Angew. Chem. Int. Ed. 2012, 51, 9372;
103. Angew. Chem. 2012, 124, 9506;
104. T. K. Hyster, L. Knoerr, T. R. Ward, T. Rovis, Science 2012, 338, 500;
105. B. Ye, N. Cramer, Science 2012, 338, 504;
106. G. Liu, Y. Shen, Z. Zhou, X. Lu, Angew. Chem. Int. Ed. 2013, 52, 6033;
107. Angew. Chem. 2013, 125, 6149; ruthenium:
108. L. Ackermann, S. Fenner, Org. Lett. 2011, 13, 6548;
109. R. K. Chinnagolla, S. Pimparkar, M. Jeganmohan, Org. Lett. 2012, 14, 3032.
110. D. Zhao, Z. Shi, F. Glorius, Angew. Chem. Int. Ed. 2013, 52, 12426;
111. Angew. Chem. 2013, 125, 12652; recent examples of rhodium-catalyzed C-H activation including an N-N bond cleavage:
112. B. Liu, C. Song, C. Sun, S. Zhou, J. Zhu, J. Am. Chem. Soc. 2013, 135, 16625;
113. C. Wang, Y. Huang, Org. Lett. 2013, 15, 5294;
114. L. Zheng, R. Hua, Chem. Eur. J. 2014, 20, 2352;
115. K. Muralirajan, C.-H. Cheng, Adv. Synth. Catal. 2014, 356, 1571.
116. W.-J. Chen, Z. Lin, Organometallics 2015, 34, 309.
117. D. Zhao, S. Vásquez-Céspedes, F. Glorius, Angew. Chem. Int. Ed. 2015, 54, 1657;
118. Angew. Chem. 2015, 127, 1677.
119. J. Li, Z. Qiu, J. Org. Chem. 2015, 80, 10686.