Iridium-Catalyzed Intramolecular Asymmetric Allylic Dearomatization Reaction of Pyridines, Pyrazines, Quinolines, and Isoquinolines

Journal of the American Chemical Society

Volumn 137, Issue 50, 2015, Pages 15899-15906

  Yang, Ze Peng ^a   Wu, Qing Feng ^a   Shao, Wen ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; CATALYSIS; IRIDIUM; LIGANDS; PYRIDINE; STEREOCHEMISTRY;

ALTERNATIVE PROCESS; DEAROMATIZATION; FORMAL SYNTHESIS; ISOQUINOLINES; MECHANISTIC STUDIES; PYRAZINES;

REACTION INTERMEDIATES;

GEPHYROTOXIN; IRIDIUM; ISOQUINOLINE DERIVATIVE; LIGAND; PYRAZINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; FEASIBILITY STUDY; REACTION ANALYSIS; SYNTHESIS; CHEMISTRY; CYCLIZATION;

CATALYSIS; CYCLIZATION; IRIDIUM; PYRAZINES; PYRIDINES; QUINOLINES;

EID: 84952780474     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b10440     Document Type: Article

References (130)

1. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4 th ed.; Blackwell Science: Oxford, U.K., 2000.
2. Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917 10.1021/cr9902852
3. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068 10.1002/anie.201006017
4. Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 12662 10.1002/anie.201204822
5. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 10.1021/cr9409804
6. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921 10.1021/cr020027w
7. Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258 10.1002/anie.200605113
8. Weaver, J. D.; Recio, A., III; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846 10.1021/cr1002744
9. Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558 10.1021/ar500167f
10. Wu, Q.-F.; He, H.; Liu, W.-B.; You, S.-L. J. Am. Chem. Soc. 2010, 132, 11418 10.1021/ja105111n
11. Wu, Q.-F.; Liu, W.-B.; Zhuo, C.-X.; Rong, Z.-Q.; Ye, K.-Y.; You, S.-L. Angew. Chem., Int. Ed. 2011, 50, 4455 10.1002/anie.201100206
12. Wu, Q.-F.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 1680 10.1002/anie.201107677
13. Zhuo, C.-X.; Liu, W.-B.; Wu, Q.-F.; You, S.-L. Chem. Sci. 2012, 3, 205 10.1039/C1SC00517K
14. Zhuo, C.-X.; You, S.-L. Angew. Chem., Int. Ed. 2013, 52, 10056 10.1002/anie.201304591
15. Zhang, X.; Han, L.; You, S.-L. Chem. Sci. 2014, 5, 1059 10.1039/c3sc53019a
16. Zhuo, C.-X.; Zhou, Y.; You, S.-L. J. Am. Chem. Soc. 2014, 136, 6590 10.1021/ja5028138
17. Zhuo, C.-X.; Cheng, Q.; Liu, W.-B.; Zhao, Q.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 8475 10.1002/anie.201502259
18. Zhang, X.; Liu, W.-B.; Tu, H.-F.; You, S.-L. Chem. Sci. 2015, 6, 4525 10.1039/C5SC01772F
19. Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314 10.1021/ja0608139
20. Yoshida, M.; Nemoto, T.; Zhao, Z.; Ishige, Y.; Hamada, Y. Tetrahedron: Asymmetry 2012, 23, 859 10.1016/j.tetasy.2012.05.026
21. Liu, Y.; Du, H. Org. Lett. 2013, 15, 740 10.1021/ol3032736
22. Kaiser, T. M.; Yang, J. Eur. J. Org. Chem. 2013, 2013, 3983 10.1002/ejoc.201300515
23. Trost, B. M.; Ehmke, V.; O'Keefe, B. M.; Bringley, D. A. J. Am. Chem. Soc. 2014, 136, 8213 10.1021/ja5044825
24. Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592 10.1021/ja0501161
25. Kagawa, N.; Malerich, J. P.; Rawal, V. Org. Lett. 2008, 10, 2381 10.1021/ol8006277
26. Chen, J.; Cook, M. J. Org. Lett. 2013, 15, 1088 10.1021/ol400110c
27. Montgomery, T. D.; Zhu, Y.; Kagawa, N.; Rawal, V. H. Org. Lett. 2013, 15, 1140 10.1021/ol400334u
28. Kielland, N.; Lavilla, R. Top. Heterocycl. Chem. 2010, 25, 127 10.1007/7081-2010-42
29. Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327 10.1021/ja0010352
30. Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784 10.1021/ja016935c
31. Ichikawa, E.; Suzuki, M.; Yabu, K.; Albert, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 11808 10.1021/ja045966f
32. Frisch, K.; Landa, A.; Saaby, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 6058 10.1002/anie.200501900
33. Yamaoka, Y.; Miyabe, H.; Takemoto, Y. J. Am. Chem. Soc. 2007, 129, 6686 10.1021/ja071470x
34. Sun, Z.; Yu, S.; Ding, Z.; Ma, D. J. Am. Chem. Soc. 2007, 129, 9300 10.1021/ja0734849
35. Christian, C.; Aly, S.; Belyk, K. J. Am. Chem. Soc. 2011, 133, 2878 10.1021/ja111540g
36. Hashimoto, T.; Omote, M.; Maruoka, K. Angew. Chem., Int. Ed. 2011, 50, 3489 10.1002/anie.201100331
37. Hashimoto, T.; Omote, M.; Maruoka, K. Angew. Chem., Int. Ed. 2011, 50, 8952 10.1002/anie.201104017
38. Zhou, Y.-Y.; Li, J.; Ling, L.; Liao, S.-H.; Sun, X.-L.; Li, Y.-X.; Wang, L.-J.; Tang, Y. Angew. Chem., Int. Ed. 2013, 52, 1452 10.1002/anie.201207576
39. Ishida, T.; Ikota, H.; Kurahashi, K.; Tsukano, C.; Takemoto, Y. Angew. Chem., Int. Ed. 2013, 52, 10204 10.1002/anie.201305581
40. Xu, X.; Zavalij, P. Y.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 12439 10.1021/ja406482q
41. García Mancheno, O.; Asmus, S.; Zurro, M.; Fischer, T. Angew. Chem., Int. Ed. 2015, 54, 8823 10.1002/anie.201502708
42. Dyson, P. J. Dalton Trans. 2003, 2964 10.1039/b303250g
43. Glorius, F. Org. Biomol. Chem. 2005, 3, 4171 10.1039/b512139f
44. Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357 10.1021/ar700094b
45. Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557 10.1021/cr200328h
46. Yu, Z.; Jin, W.; Jiang, Q. Angew. Chem., Int. Ed. 2012, 51, 6060 10.1002/anie.201200963
47. He, Y.-M.; Song, F.-T.; Fan, Q.-H. Top. Curr. Chem. 2014, 343, 145 10.1007/128-2013-480
48. Ye, Z.-S.; Shi, L.; Zhou, Y.-G. Synlett 2014, 25, 928 10.1055/s-0033-1341029
49. Urban, S.; Ortega, N.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 3803 10.1002/anie.201100008
50. Chen, Q.-A.; Wang, D.-S.; Zhou, Y.-G.; Duan, Y.; Fan, H.-J.; Yang, Y.; Zhang, Z. J. Am. Chem. Soc. 2011, 133, 6126 10.1021/ja200723n
51. Chen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2012, 134, 2442 10.1021/ja211684v
52. Kuwano, R.; Morioka, R.; Kashiwabara, M.; Kameyama, N. Angew. Chem., Int. Ed. 2012, 51, 4136 10.1002/anie.201201153
53. Iimuro, A.; Yamaji, K.; Kandula, S.; Nagano, T.; Kita, Y.; Mashima, K. Angew. Chem., Int. Ed. 2013, 52, 2046 10.1002/anie.201207748
54. Wang, T.; Chen, F.; Qin, J.; He, Y.-M.; Fan, Q.-H. Angew. Chem., Int. Ed. 2013, 52, 7172 10.1002/anie.201301830
55. Liu, Y.; Du, H. J. Am. Chem. Soc. 2013, 135, 12968 10.1021/ja406761j
56. Duan, Y.; Li, L.; Chen, M.-W.; Yu, C.-B.; Fan, H.-J.; Zhou, Y.-G. J. Am. Chem. Soc. 2014, 136, 7688 10.1021/ja502020b
57. Wysocki, J.; Ortega, N.; Glorius, F. Angew. Chem., Int. Ed. 2014, 53, 8751 10.1002/anie.201310985
58. Chang, M.; Huang, Y.; Liu, S.; Chen, Y.; Krska, S. W.; Davies, I. W.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 12761 10.1002/anie.201406762
59. Zhang, Z.; Du, H. Angew. Chem., Int. Ed. 2015, 54, 623 10.1002/anie.201409471
60. Chen, Z.-P.; Chen, M.-W.; Shi, L.; Yu, C.-B.; Zhou, Y.-G. Chem. Sci. 2015, 6, 3415 10.1039/C5SC00835B
61. Adolfsson, H. Angew. Chem., Int. Ed. 2005, 44, 3340 10.1002/anie.200500827
62. You, S.-L. Chem.-Asian J. 2007, 2, 820 10.1002/asia.200700081
63. Ouellet, S. G.; Walji, A. M.; MacMillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327 10.1021/ar7001864
64. Wang, C.; Wu, X.; Xiao, J. Chem.-Asian J. 2008, 3, 1750 10.1002/asia.200800196
65. Rueping, M.; Dufour, J.; Schoepke, F. R. Green Chem. 2011, 13, 1084 10.1039/c1gc15027h
66. Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498 10.1039/c1cs15268h
67. Wang, D.; Astruc, D. Chem. Rev. 2015, 115, 6621 10.1021/acs.chemrev.5b00203
68. Gutsulyak, D. V.; van der Est, A.; Nikonov, G. I. Angew. Chem., Int. Ed. 2011, 50, 1384 10.1002/anie.201006135
69. Königs, C. D. F.; Klare, H. F. T.; Oestreich, M. Angew. Chem., Int. Ed. 2013, 52, 10076 10.1002/anie.201305028
70. Arrowsmith, M.; Hill, M. S.; Hadlington, T.; Kociok-Köhn, G.; Weetman, C. Organometallics 2011, 30, 5556 10.1021/om2008138
71. Oshima, K.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2012, 134, 3699 10.1021/ja3002953
72. Dudnik, A. S.; Weidner, V. L.; Motta, A.; Delferro, M.; Marks, T. J. Nat. Chem. 2014, 6, 1100 10.1038/nchem.2087
73. Fan, X.; Zheng, J.; Li, Z. H.; Wang, H. J. Am. Chem. Soc. 2015, 137, 4916 10.1021/jacs.5b03147
74. Yang, Z.-P.; Wu, Q.-F.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 6986 10.1002/anie.201404286
75. Miyabe, H.; Takemoto, Y. Synlett 2005, 1641 10.1055/s-2005-869871
76. Takeuchi, R.; Kezuka, S. Synthesis 2006, 2006, 3349 10.1055/s-2006-950284
77. Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675 10.1039/B614169B
78. Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461 10.1021/ar100047x
79. Hartwig, J. F.; Pouy, M. J. Top. Organomet. Chem. 2011, 34, 169 10.1007/978-3-642-15334-17
80. Liu, W.-B.; Xia, J.-B.; You, S.-L. Top. Organomet. Chem. 2011, 38, 155 10.1007/3418-2011-10
81. Tosatti, P.; Nelson, A.; Marsden, S. P. Org. Biomol. Chem. 2012, 10, 3147 10.1039/c2ob07086c
82. Helmchen, G. In Molecular Catalysis; Gade, L. H.; Hofmann, P., Eds.; Wiley-VCH: Weinheim, 2014; pp 235-254.
83. Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797 10.1002/anie.200460276
84. Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 15249 10.1021/ja306850b
85. Roggen, M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 8652 10.1002/anie.201202092
86. Schafroth, M. A.; Sarlah, D.; Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2012, 134, 20276 10.1021/ja310386m
87. Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 994 10.1021/ja311422z
88. Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2068 10.1021/ja311363a
89. Liu, W.-B.; Reeves, C. M.; Virgil, S. C.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 10626 10.1021/ja4052075
90. Liu, W.-B.; Reeves, C. M.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 17298 10.1021/ja4097829
91. Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065 10.1126/science.1237068
92. Qu, J.; Roßberg, L.; Helmchen, G. J. Am. Chem. Soc. 2014, 136, 1272 10.1021/ja411869r
93. Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3006 10.1021/ja412962w
94. Krautwald, S.; Schafroth, M. A.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020 10.1021/ja5003247
95. Zhang, X.; Yang, Z.-P.; Huang, L.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 1873 10.1002/anie.201409976
96. Breitler, S.; Carreira, E. M. J. Am. Chem. Soc. 2015, 137, 5296 10.1021/jacs.5b01951
97. Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 7644 10.1002/anie.201501851
98. Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953 10.1016/S0040-4020(03)00295-3
99. Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Chem. Rev. 2011, 111, 7157 10.1021/cr100307m
100. Duttwyler, S.; Lu, C.; Rheingold, A. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2012, 134, 4064 10.1021/ja2119833
101. Ischay, M. A.; Takase, M. K.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 2478 10.1021/ja312311k
102. Duttwyler, S.; Chen, S.; Takase, M. K.; Wiberg, K. B.; Bergman, R. G.; Ellman, J. A. Science 2013, 339, 678 10.1126/science.1230704
103. Duttwyler, S.; Chen, S.; Lu, C.; Mercado, B. Q.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2014, 53, 3877 10.1002/anie.201310517
104. Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Synthesis 2009, 2009, 2076 10.1055/s-0029-1216823
105. Liu, W.-B.; Zheng, C.; Zhuo, C.-X.; Dai, L.-X.; You, S.-L. J. Am. Chem. Soc. 2012, 134, 4812 10.1021/ja210923k
106. Wang, M.; Wang, Z.; Shi, Y.-H.; Shi, X.-X.; Fossey, J. S.; Deng, W.-P. Angew. Chem., Int. Ed. 2011, 50, 4897 10.1002/anie.201007960
107. Wang, Z.; Ye, J.; Wu, R.; Liu, Y.-Z.; Fossey, J. S.; Cheng, J.; Deng, W.-P. Catal. Sci. Technol. 2014, 4, 1909 10.1039/c3cy00904a
108. Jiang, S.-S.; Gu, B.-Q.; Zhu, M.-Y.; Yu, X.; Deng, W.-P. Tetrahedron 2015, 71, 1187 10.1016/j.tet.2015.01.018
109. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456 10.1021/ar00156a004
110. Zhao, X.; Liu, D.; Guo, H.; Liu, Y.; Zhang, W. J. Am. Chem. Soc. 2011, 133, 19354 10.1021/ja209373k
111. Daly, J. W.; Witkop, B.; Tokuyama, T.; Nishikawa, T.; Karle, I. L. Helv. Chim. Acta 1977, 60, 1128 10.1002/hlca.19770600336
112. Daly, J. W. Fortschr. Chem. Org. Naturst. 1982, 41, 205 10.1007/978-3-7091-8656-5-6
113. Souccar, C.; Varanda, W. A.; Daly, J. W.; Albuquerque, E. X. Mol. Pharmacol. 1984, 25, 384
114. Souccar, C.; Varanda, W. A.; Aronstam, R. S.; Daly, J. W.; Albuquerque, E. X. Mol. Pharmacol. 1984, 25, 395
115. Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454 10.1021/ja00524a057
116. Fujimoto, R.; Kishi, Y.; Blount, J. F. J. Am. Chem. Soc. 1980, 102, 7154 10.1021/ja00543a067
117. Hart, D. J. J. Org. Chem. 1981, 46, 3576 10.1021/jo00330a051
118. Fujimoto, R.; Kishi, Y. Tetrahedron Lett. 1981, 22, 4197 10.1016/S0040-4039(01)82102-X
119. Hart, D. J.; Kanai, K. J. Am. Chem. Soc. 1983, 105, 1255 10.1021/ja00343a030
120. Overman, L. E.; Lesuisse, D.; Hashimoto, M. J. Am. Chem. Soc. 1983, 105, 5373 10.1021/ja00354a031
121. Shirokane, K.; Wada, T.; Yoritate, M.; Minamikawa, R.; Takayama, N.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2014, 53, 512 10.1002/anie.201308905
122. Chu, S.; Wallace, S.; Smith, M. D. Angew. Chem., Int. Ed. 2014, 53, 13826 10.1002/anie.201409038
123. Ito, Y.; Nakajo, E.; Nakatsuka, M.; Saegusa, T. Tetrahedron Lett. 1983, 24, 2881 10.1016/S0040-4039(00)88049-1
124. Pearson, W. H.; Fang, W.-K. J. Org. Chem. 2000, 65, 7158 10.1021/jo0011383
125. Wei, L.-L.; Hsung, R. P.; Sklenicka, H. M.; Gerasyuto, A. I. Angew. Chem., Int. Ed. 2001, 40, 1516 10.1002/1521-3773(20010417)40:8<1516::AID-ANIE1516>3.0.CO;2-V
126. Santarem, M.; Vanucci-Bacqué, C.; Lhommet, G. J. Org. Chem. 2008, 73, 6466 10.1021/jo801150e
127. Miao, L.; Shu, H.; Noble, A. R.; Fournet, S. P.; Stevens, E. D.; Trudell, M. L. ARKIVOC 2010, 2010, 6
128. Pichette, S.; Winter, D. K.; Lessard, J.; Spino, C. J. Org. Chem. 2013, 78, 12532 10.1021/jo402217e
129. Ortega, N.; Tang, D.-T. D.; Urban, S.; Zhao, D.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 9500 10.1002/anie.201302218
130. Barton, D. H. R.; Samadi, M. Tetrahedron 1992, 48, 7083 10.1016/S0040-4020(01)88249-1