The nickel(II)-catalyzed direct benzylation, allylation, alkylation, and methylation of C-H bonds in aromatic amides containing an 8-aminoquinoline moiety as the directing group

Bulletin of the Chemical Society of Japan

Volumn 88, Issue 3, 2015, Pages 438-446

  Aihara, Yoshinori ^a   Wuelbern, Jendrik ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; FUNCTIONAL GROUPS; NICKEL;

8-AMINOQUINOLINE; ALKYLATION REACTIONS; CATALYZED REACTIONS; DIRECT ALKYLATION; DIRECTING GROUPS; ELECTRONIC NATURES; ELECTROPHILIC COUPLING; SUBSTITUTED AROMATIC;

ALKYLATION;

EID: 84925426356     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20140387     Document Type: Article

References (87)

1. a) F. Kakiuchi, T. Kochi, Synthesis 2008, 3013.
2. b) D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624.
3. c) O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074.
4. d) T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147.
5. e) P. Sehnal, R. J. K. Taylor, I. J. S. Fairlamb, Chem. Rev. 2010, 110, 824.
6. f) M. Wasa, K. M. Engle, J.-Q. Yu, Isr. J. Chem. 2010, 50, 605.
7. g) L.-M. Xu, B.-J. Li, Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712.
8. h) D. Y.-K. Chen, S. W. Youn, Chem. - Eur. J. 2012, 18, 9452.
9. i) N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem., Int. Ed. 2012, 51, 10236.
10. j) J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem., Int. Ed. 2012, 51, 8960.
11. k) B. Li, P. H. Dixneuf, Chem. Soc. Rev. 2013, 42, 5744.
12. l) M. Corbet, F. De Campo, Angew. Chem., Int. Ed. 2013, 52, 9896.
13. m) G. Rouquet, N. Chatani, Angew. Chem., Int. Ed. 2013, 52, 11726.
14. n) J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369.
15. o) K. Gao, N. Yoshikai, Acc. Chem. Res. 2014, 47, 1208.
16. p) Z. Huang, G. Dong, Tetrahedron Lett. 2014, 55, 5869.
17. q) L. C. Misal Castro, N. Chatani, Chem. Lett. 2015, in press. doi:10.1246/cl.150024.
18. a) S. Messaoudi, J.-D. Brion, M. Alami, Eur. J. Org. Chem. 2010, 6495.
19. b) L. Ackermann, Chem. Commun. 2010, 46, 4866.
20. c) L. Ackermann, J. Org. Chem. 2014, 79, 8948.
21. M. B. Smith, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley & Sons, 2013.
22. a) S. J. Tremont, R. U. Hayat, J. Am. Chem. Soc. 1984, 106, 5759.
23. b) Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, Angew. Chem., Int. Ed. 2009, 48, 6097.
24. c) D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965.
25. d) M.-J. Jang, S.-W. Youn, Bull. Korean Chem. Soc. 2011, 32, 2865.
26. e) Y. Zhao, G. Chen, Org. Lett. 2011, 13, 4850.
27. f) L. D. Tran, O. Daugulis, Angew. Chem., Int. Ed. 2012, 51, 5188.
28. g) K. Chen, F. Hu, S.-Q. Zhang, B.-F. Shi, Chem. Sci. 2013, 4, 3906.
29. h) S.-Y. Zhang, G. He, W. A. Nack, Y. Zhao, Q. Li, G. Chen, J. Am. Chem. Soc. 2013, 135, 2124.
30. i) S.-Y. Zhang, Q. Li, G. He, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2013, 135, 12135.
31. j) B. Xiao, Z.-J. Liu, L. Liu, Y. Fu, J. Am. Chem. Soc. 2013, 135, 616.
32. k) R.-Y. Zhu, J. He, X.-C. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 13194.
33. l) K. Chen, B.-F. Shi, Angew. Chem., Int. Ed. 2014, 53, 11950.
34. m) S.-Y. Zhang, Q. Li, G. He, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2015, 137, 531.
35. L. Ackermann, P. Novák, R. Vicente, N. Hofmann, Angew. Chem., Int. Ed. 2009, 48, 6045.
36. a) E. R. Fruchey, B. M. Monks, S. P. Cook, J. Am. Chem. Soc. 2014, 136, 13130.
37. b) L. Ilies, T. Matsubara, S. Ichikawa, S. Asako, E. Nakamura, J. Am. Chem. Soc. 2014, 136, 13126.
38. c) B. M. Monks, E. R. Fruchey, S. P. Cook, Angew. Chem., Int. Ed. 2014, 53, 11065.
39. a) Q. Chen, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2011, 133, 428.
40. b) K. Gao, N. Yoshikai, J. Am. Chem. Soc. 2013, 135, 9279.
41. c) B. Punji, W. Song, G. A. Shevchenko, L. Ackermann, Chem. - Eur. J. 2013, 19, 10605.
42. d) K. Gao, T. Yamakawa, N. Yoshikai, Synthesis 2014, 46, 2024.
43. Y. Aihara, N. Chatani, J. Am. Chem. Soc. 2013, 135, 5308.
44. a) X. Wu, Y. Zhao, H. Ge, J. Am. Chem. Soc. 2014, 136, 1789.
45. b) W. Song, S. Lackner, L. Ackermann, Angew. Chem., Int. Ed. 2014, 53, 2477.
46. c) X. Cong, Y. Li, Y. Wei, X. Zeng, Org. Lett. 2014, 16, 3926.
47. a) S. Inoue, H. Shiota, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2009, 131, 6898.
48. b) N. Hasegawa, V. Charra, S. Inoue, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2011, 133, 8070.
49. c) H. Shiota, Y. Ano, Y. Aihara, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2011, 133, 14952.
50. d) N. Hasegawa, K. Shibata, V. Charra, S. Inoue, Y. Fukumoto, N. Chatani, Tetrahedron 2013, 69, 4466.
51. a) Y. Ano, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 2011, 133, 12984.
52. b) Y. Aihara, N. Chatani, Chem. Sci. 2013, 4, 664.
53. c) G. Rouquet, N. Chatani, Chem. Sci. 2013, 4, 2201.
54. d) Y. Aihara, N. Chatani, J. Am. Chem. Soc. 2014, 136, 898.
55. e) K. Shibata, N. Chatani, Org. Lett. 2014, 16, 5148.
56. f) Y. Aihara, M. Tobisu, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2014, 136, 15509.
57. g) M. Al-Amin, M. Arisawa, S. Shuto, Y. Ano, M. Tobisu, N. Chatani, Adv. Synth. Catal. 2014, 356, 1631.
58. h) A. Yokota, Y. Aihara, N. Chatani, J. Org. Chem. 2014, 79, 11922.
59. i) M. Iyanaga, Y. Aihara, N. Chatani, J. Org. Chem. 2014, 79, 11933.
60. j) T. Uemura, T. Igarashi, M. Noguchi, K. Shibata, N. Chatani, Chem. Lett. 2015, in press. doi:10.1246/cl.150041.
61. Our preliminary paper (ref 8) reported that only traces of 34 are produced, but the yield was improved to 61% when NaI was added to the reaction mixture. However, this is an error and the data shown in Table 4 show the correct values.
62. M. F. Semmelhack, P. M. Helquist, L. D. Jones, J. Am. Chem. Soc. 1971, 93, 5908.
63. D. Griller, K. U. Ingold, Acc. Chem. Res. 1980, 13, 317.
64. a) R. J. Kinney, W. D. Jones, R. G. Bergman, J. Am. Chem. Soc. 1978, 100, 7902.
65. b) C. E. Ash, P. W. Hurd, M. Y. Darensbourg, M. Newcomb, J. Am. Chem. Soc. 1987, 109, 3313.
66. c) S. Biswas, D. J. Weix, J. Am. Chem. Soc. 2013, 135, 16192.
67. d) J. Breitenfeld, J. Ruiz, M. D. Wodrich, X. Hu, J. Am. Chem. Soc. 2013, 135, 12004.
68. e) J. Choi, P. Martín-Gago, G. C. Fu, J. Am. Chem. Soc. 2014, 136, 12161.
69. f) C. Zhao, X. Jia, X. Wang, H. Gong, J. Am. Chem. Soc. 2014, 136, 17645.
70. a) J. Terao, N. Kambe, Acc. Chem. Res. 2008, 41, 1545.
71. b) A. T. Higgs, P. J. Zinn, M. S. Sanford, Organometallics 2010, 29, 5446.
72. c) B. Zheng, F. Tang, J. Luo, J. W. Schultz, N. P. Rath, L. M. Mirica, J. Am. Chem. Soc. 2014, 136, 6499.
73. H. Schönherr, T. Cernak, Angew. Chem., Int. Ed. 2013, 52, 12256.
74. J. S. McCallum, J. R. Gasdaska, L. S. Liebeskind, S. J. Tremont, Tetrahedron Lett. 1989, 30, 4085.
75. a) C. Verrier, C. Hoarau, F. Marsais, Org. Biomol. Chem. 2009, 7, 647.
76. b) S.-Y. Zhang, G. He, W. A. Nack, Y. Zhao, Q. Li, G. Chen, J. Am. Chem. Soc. 2013, 135, 2124.
77. c) L. C. Misal Castro, N. Chatani, Chem. - Eur. J. 2014, 20, 4548.
78. a) X. Chen, J.-J. Li, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 78.
79. b) R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510.
80. c) H.-X. Dai, A. F. Stepan, M. S. Plummer, Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 7222.
81. d) S. R. Neufeldt, C. K. Seigerman, M. S. Sanford, Org. Lett. 2013, 15, 2302.
82. e) B. R. Rosen, L. R. Simke, P. S. Thuy-Boun, D. D. Dixon, J.-Q. Yu, P. S. Baran, Angew. Chem., Int. Ed. 2013, 52, 7317.
83. Y. Zhang, J. Feng, C.-J. Li, J. Am. Chem. Soc. 2008, 130, 2900.
84. a) Q. Chen, L. Ilies, N. Yoshikai, E. Nakamura, Org. Lett. 2011, 13, 3232.
85. b) B. Yao, R.-J. Song, Y. Liu, Y.-X. Xie, J.-H. Li, M.-K. Wang, R.-Y. Tang, X.-G. Zhang, C.-L. Deng, Adv. Synth. Catal. 2012, 354, 1890.
86. c) F. Pan, Z.-Q. Lei, H. Wang, H. Li, J. Sun, Z.-J. Shi, Angew. Chem., Int. Ed. 2013, 52, 2063.
87. d) J. Gui, Q. Zhou, C.-M. Pan, Y. Yabe, A. C. Burns, M. R. Collins, M. A. Ornelas, Y. Ishihara, P. S. Baran, J. Am. Chem. Soc. 2014, 136, 4853.