Regioselective introduction of heteroatoms at the C-8 position of quinoline N-oxides: Remote C-H activation using N-oxide as a stepping stone

Journal of the American Chemical Society

Volumn 136, Issue 30, 2014, Pages 10770-10776

  Hwang, Heejun ^a,b   Kim, Jinwoo ^a,b   Jeong, Jisu ^a,b   Chang, Sukbok ^a,b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Institute for Basic Science   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL ACTIVATION; FUNCTIONAL GROUPS;

ACID ADDITIVES; C-H FUNCTIONALIZATION; CATALYTIC SYSTEM; DIRECTING GROUPS; EFFICIENT SYNTHESIS; MECHANISTIC STUDIES; METAL-CATALYZED; REGIO-SELECTIVE;

REGIOSELECTIVITY;

ACID; ESTER DERIVATIVE; FUNCTIONAL GROUP; IRIDIUM; METAL; OXIDE; QUINOLINE DERIVATIVE; RHODIUM; AMIDE; QUINOLINE;

AMIDATION; ARTICLE; CATALYSIS; CATALYST; IODINATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; STEREOISOMERISM;

AMIDES; CATALYSIS; HALOGENATION; IRIDIUM; MODELS, MOLECULAR; OXIDES; QUINOLINES; RHODIUM; STEREOISOMERISM;

EID: 84905233935     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5053768     Document Type: Article

References (104)

1. Egan, T. J.; Ross, D. C.; Adams, P. A. FEBS Lett. 1994, 352, 54
2. Foley, M.; Tilley, L. Pharmacol. Ther. 1998, 79, 55
3. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2003.
4. Michael, J. P. Nat. Prod. Rep. 2008, 25, 166
5. Solomon, V. R.; Lee, H. Curr. Med. Chem. 2011, 18, 1488
6. Hughes, G.; Bryce, M. R. J. Mater. Chem. 2005, 15, 94
7. Kimyonok, A.; Wang, X. Y.; Weck, M. Polym. Rev. 2006, 46, 47
8. Chemistry of Heterocyclic Compounds: Quinolines; Jones, G., Ed.; Wiley: Chichester, U.K., 1977, (Part I), 1982, (Part II), 1990, (Part III); Vol. 32.
9. Mongin, F.; Queguiner, G. Tetrahedron 2001, 57, 4059
10. Youssef, M. S. K.; Ahmed, R. A. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 1123
11. Mphahlele, M. J.; Lesenyeho, L. G. J. Heterocycl. Chem. 2013, 50, 1
12. Madapa, S.; Tusi, Z.; Batra, S. Curr. Org. Chem. 2008, 12, 1116
13. Marco-Contelles, J.; Pérez-Mayoral, E.; Samadi, A.; Carreiras, M. d. C.; Soriano, E. Chem. Rev. 2009, 109, 2652
14. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077
15. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
16. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
17. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
18. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
19. Ackermann, L. Chem. Rev. 2011, 111, 1315
20. Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588
21. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
22. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
23. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
24. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
25. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
26. Satoh, T.; Miura, M. Synthesis-Stuttgart 2010, 2010, 3395
27. Daugulis, O.; Do, H. Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
28. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
29. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
30. White, M. C. Science 2012, 335, 807
31. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
32. Hyster, T. K.; Knörr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500
33. Black, D. A.; Beveridge, R. E.; Arndtsen, B. A. J. Org. Chem. 2008, 73, 1906
34. Deng, G. J.; Li, C. J. Org. Lett. 2009, 11, 1171
35. Ye, W. J.; Luo, N.; Yu, Z. K. Organometallics 2010, 29, 1049
36. Berman, A. M.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2010, 75, 7863
37. Wen, P.; Li, Y.; Zhou, K.; Ma, C.; Lan, X.; Ma, C.; Huang, G. Adv. Synth. Catal. 2012, 354, 2135
38. Ren, X. Y.; Wen, P.; Shi, X. K.; Wang, Y. L.; Li, J.; Yang, S. Z.; Yan, H.; Huang, G. S. Org. Lett. 2013, 15, 5194
39. Kanyiva, K. S.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2007, 46, 8872
40. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254
41. Wu, J. L.; Cui, X. L.; Chen, L. M.; Jiang, G. J.; Wu, Y. J. J. Am. Chem. Soc. 2009, 131, 13888
42. Campeau, L.-C.; Stuart, D. R.; Leclerc, J.-P.; Bertrand-Laperle, M.; Villemure, E.; Sun, H.-Y.; Lasserre, S.; Guimond, N.; Lecavallier, M.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 3291
43. Araki, Y.; Kobayashi, K.; Yonemoto, M.; Kondo, Y. Org. Biomol. Chem. 2011, 9, 78
44. Ryu, J.; Cho, S. H.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 3677
45. Wu, Z. Y.; Pi, C.; Cui, X. L.; Bai, J.; Wu, Y. J. Adv. Synth. Catal. 2013, 355, 1971
46. Chen, X.; Zhu, C.; Cui, X.; Wu, Y. Chem. Commun. 2013, 49, 6900
47. Li, G.; Jia, C. Q.; Sun, K. Org. Lett. 2013, 15, 5198
48. Kwak, J.; Kim, M.; Chang, S. J. Am. Chem. Soc. 2011, 133, 3780
49. Konishi, S.; Kawamorita, S.; Iwai, T.; Steel, P. G.; Marder, T. B.; Sawamura, M. Chem. Asian J. 2014, 9, 434
50. Shibata, T.; Matsuo, Y. Adv. Synth. Catal. 2014, 356, 1516
51. Frederickson, C. J.; Kasarskis, E. J.; Ringo, D.; Frederickson, R. E. J. Neurosci. Methods 1987, 20, 91
52. Chen, B. Z.; Dodge, M. E.; Tang, W.; Lu, J. M.; Ma, Z. Q.; Fan, C. W.; Wei, S. G.; Hao, W. N.; Kilgore, J.; Williams, N. S.; Roth, M. G.; Amatruda, J. F.; Chen, C.; Lum, L. Nat. Chem. Biol. 2009, 5, 100
53. Harkins, S. B.; Peters, J. C. Organometallics 2002, 21, 1753
54. Yoon, J.; Wilson, S. A.; Jang, Y. K.; Seo, M. S.; Nehru, K.; Hedman, B.; Hodgson, K. O.; Bill, E.; Solomon, E. I.; Nam, W. Angew. Chem., Int. Ed. 2009, 48, 1257
55. Yakushchenko, I. K.; Kaplunov, M. G.; Krasnikova, S. S.; Roshchupkina, O. S.; Pivovarov, A. P. Russ. J. Coord. Chem. 2009, 35, 312
56. Makida, Y.; Ohmiya, H.; Sawamura, M. Chem. Asian J. 2011, 6, 410
57. Hitomi, Y.; Hiramatsu, K.; Arakawa, K.; Takeyasu, T.; Hata, M.; Kodera, M. Dalton Trans. 2013, 42, 12878
58. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
59. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
60. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984
61. Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2013, 135, 12135
62. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
63. Krishnan, V.; Patel, C. C. Can. J. Chem. 1966, 44, 972
64. Hatfield, W. E.; Copley, D. B.; Whyman, R. Inorg. Nucl. Chem. Lett. 1966, 2, 373
65. Nelson, J. H.; Nathan, L. C.; Ragsdale, R. O. Inorg. Chem. 1968, 7, 1840
66. Nathan, L. C.; Ragsdale, R. O. Inorg. Chim. Acta 1969, 3, 473
67. Stiakaki, M. A. D.; Christofides, A. Polyhedron 1993, 12, 661
68. Andreev, V. P.; Nizhnik, Y. P.; Tunina, S. G.; Belashev, B. Z. Chem. Heterocycl. Compd. 2002, 38, 553
69. Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599
70. Yoo, B. W.; Choi, K. H.; Choi, K. I.; Kim, J. H. Synth. Commun. 2003, 33, 4185
71. Handa, Y.; Inanaga, J.; Yamaguchi, M. J. Chem. Soc., Chem. Commun. 1989, 298
72. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; Meijere, A. d.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
73. Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Tetrahedron 2006, 62, 11483
74. Schroder, N.; Wencel-Delord, J.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 8298
75. Kuhl, N.; Schroder, N.; Glorius, F. Org. Lett. 2013, 15, 3860
76. Wang, L. H.; Ackermann, L. Chem. Commun. 2014, 50, 1083
77. Mao, L.; Moriuchi, T.; Sakurai, H.; Fujii, H.; Hirao, T. Tetrahedron Lett. 2005, 46, 8419
78. Lee, C.-I.; Zhou, J.; Ozerov, O. V. J. Am. Chem. Soc. 2013, 135, 3560
79. Nifant'ev, I. E.; Ivchenko, P. V.; Bagrov, V. V.; Nagy, S. M.; Winslow, L. N.; Merrick-Mack, J. A.; Mihan, S.; Churakov, A. V. Dalton Trans. 2013, 42, 1501
80. Kang, T.; Kim, Y.; Lee, D.; Wang, Z.; Chang, S. J. Am. Chem. Soc. 2014, 136, 4141
81. Lee, D.; Kim, Y.; Chang, S. J. Org. Chem. 2013, 78, 11102
82. Ryu, J.; Kwak, J.; Shin, K.; Lee, D.; Chang, S. J. Am. Chem. Soc. 2013, 135, 12861
83. Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362
84. Liu, J. K.; Wu, X. F.; Iggo, J. A.; Xiao, J. L. Coord. Chem. Rev. 2008, 252, 782
85. Engelman, K. L.; Feng, Y. E.; Ison, E. A. Organometallics 2011, 30, 4572
86. Frasco, D. A.; Lilly, C. P.; Boyle, P. D.; Ison, E. A. ACS Catal. 2013, 3, 2421
87. Itoh, M.; Hirano, K.; Satoh, T.; Shibata, Y.; Tanaka, K.; Miura, M. J. Org. Chem. 2013, 78, 1365
88. Pan, S.; Wakaki, T.; Ryu, N.; Shibata, T. Chem. Asian J. 2014, 9, 1257
89. Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780
90. Brown, B. R.; Firth, W. J., III; Yielding, L. W. Mutat. Res. 1980, 72, 373
91. Borrero, N. V.; Bai, F.; Perez, C.; Duong, B. Q.; Rocca, J. R.; Jin, S.; Huigens, R. W., III Org. Biomol. Chem. 2014, 12, 881
92. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066
93. Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
94. For a rhodacycle obtained from N, N -dimethylaniline N -oxide, see: Huang, X.; Huang, J.; Du, C.; Zhang, X.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52, 12970
95. Kim, J. Y.; Park, S. H.; Ryu, J.; Hwan, S. C.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2012, 134, 9110
96. Kim, J.; Chang, S. Angew. Chem., Int. Ed. 2014, 53, 2203
97. Park, S. H.; Kwak, J.; Shin, K.; Ryu, J.; Park, Y.; Chang, S. J. Am. Chem. Soc. 2014, 136, 2492
98. Zhang, L. L.; Li, L.-H.; Wang, Y.-Q.; Yang, Y.-F.; Liu, X.-Y.; Liang, Y.-M. Organometallics 2014, 33, 1905
99. Zakzeski, J.; Bell, A. T. J. Mol. Catal. A: Chem. 2009, 302, 59
100. Zakzeski, J.; Behn, A.; Head-Gordon, M.; Bell, A. T. J. Am. Chem. Soc. 2009, 131, 11098
101. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism, 3 rd ed.; Wiley: New York, 1981.
102. Jordan, R. B. Reaction Mechanisms of Inorganic and Organometallic Systems, 3 rd ed.; Oxford University Press: New York, 2007.
103. Fahrni, C. J.; O'Halloran, T. V. J. Am. Chem. Soc. 1999, 121, 11448
104. Kimber, M. C.; Mahadevan, I. B.; Lincoln, S. F.; Ward, A. D.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 8204