The Photocatalyzed Aza-Henry Reaction of N-Aryltetrahydroisoquinolines: Comprehensive Mechanism, H•- versus H+-Abstraction, and Background Reactions

Journal of the American Chemical Society

Volumn 138, Issue 36, 2016, Pages 11860-11871

  Bartling, Hanna ^a   Eisenhofer, Anna ^a   Konig, Burkhard ^a   Gschwind, Ruth M ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSTRACTING; ATOMS; CATALYSTS; ELECTRON SPIN RESONANCE SPECTROSCOPY; IONS; LIGHT SOURCES; MAGNETIC MOMENTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; REACTION KINETICS; REACTION PRODUCTS;

AEROBIC AND ANAEROBIC CONDITIONS; ANAEROBIC CONDITIONS; AZA-HENRY REACTIONS; CROSS DEHYDROGENATIVE COUPLINGS; EXPERIMENTAL CONDITIONS; MECHANISTIC PATHWAYS; NUCLEAR MAGNETIC RESONANCE(NMR); PHOTOCATALYTIC SYSTEMS;

REACTION INTERMEDIATES;

DIMER; HYDROPEROXIDE; NITROGEN; OXYGEN; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; BLUE LIGHT; CATALYST; CHEMICAL BOND; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCATALYSIS; PROTON TRANSPORT; REACTION ANALYSIS; RING OPENING;

EID: 84987776164     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b06658     Document Type: Article

References (125)

1. Li, C.-J. Acc. Chem. Res. 2009, 42 (2) 335 10.1021/ar800164n
2. Yoo, W.-J.; Li, C.-J. In Topics in Current Chemistry; Yu, J.-Q.; Shi, Z., Eds.; Springer-Verlag: Berlin, 2009; pp 281-302, DOI: 10.1007/128-2009-17.
3. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215 10.1021/cr100280d
4. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
5. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527 10.1038/nchem.687
6. Teplý, F. Collect. Czech. Chem. Commun. 2011, 76 (7) 859 10.1135/cccc2011078
7. Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687 10.1039/c2cs35203f
8. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828 10.1002/anie.201200223
9. Yoon, T. P. ACS Catal. 2013, 3, 895 10.1021/cs400088e
10. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
11. Hu, J.; Wang, J.; Nguyen, T. H.; Zheng, N. Beilstein J. Org. Chem. 2013, 9, 1977 10.3762/bjoc.9.234
12. Reckenthäler, M.; Griesbeck, A. G. Adv. Synth. Catal. 2013, 355, 2727 10.1002/adsc.201300751
13. Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387 10.1039/c3ob40137e
14. Hari, D. P.; König, B. Angew. Chem., Int. Ed. 2013, 52 (18) 4734 10.1002/anie.201210276
15. Beatty, J. W.; Stephenson, C. R. J. Acc. Chem. Res. 2015, 48, 1474 10.1021/acs.accounts.5b00068
16. Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55 (1) 36 10.1016/j.tetlet.2013.10.090
17. Murahashi, S.-I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005 10.1021/ja8017362
18. Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 8928 10.1073/pnas.0601687103
19. Li, C.-J. Acc. Chem. Res. 2009, 42 (70) 335 For mechanistic studies refer to Doyle et al.(70) and Klussmann et al.(72) 10.1021/ar800164n
20. Chiba, T.; Takata, Y. J. Org. Chem. 1977, 42 (18) 2973 10.1021/jo00438a005
21. Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103 (5) 1172 10.1021/ja00395a029
22. Baslé, O.; Borduas, N.; Dubois, P.; Chapuzet, J. M.; Chan, T.-H.; Lessard, J.; Li, C.-J. Chem.-Eur. J. 2010, 16, 8162 10.1002/chem.201000240
23. Tsang, A. S.-K.; Todd, M. H. Tetrahedron Lett. 2009, 50, 1199 10.1016/j.tetlet.2008.12.101
24. Tsang, A. S.-K.; Jensen, P.; Hook, J. M.; Hashmi, A. S. K.; Todd, M. H. Pure Appl. Chem. 2011, 83 (3) 655 10.1351/PAC-CON-11-01-01
25. Wang, H.; Li, X.; Wu, F.; Wan, B. Tetrahedron Lett. 2012, 53 (6) 681 10.1016/j.tetlet.2011.11.120
26. Zhang, G.; Ma, Y.; Wang, S.; Kong, W.; Wang, R. Chem. Sci. 2013, 4 (6) 2645 10.1039/c3sc50604e
27. Pandey, G. Tetrahedron Lett. 1988, 29 (33) 4153 10.1016/S0040-4039(00)80442-6
28. Pandey, G.; Kumaraswamy, G.; Reddy, P. Y. Tetrahedron 1992, 48 (38) 8295 10.1016/S0040-4020(01)80497-X
29. Pandey, G.; Gadre, S. R. ARKIVOC 2003, 45
30. Condie, A. G.; González-Gómez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464 10.1021/ja909145y
31. Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14 (1) 94 10.1021/ol202883v
32. Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2012, 51, 4144 10.1002/anie.201200961
33. Neumann, M.; Zeitler, K. Org. Lett. 2012, 14 (11) 2658 10.1021/ol3005529
34. To, W.-P.; Liu, Y.; Lau, T.-C.; Che, C.-M. Chem.-Eur. J. 2013, 19, 5654 10.1002/chem.201203774
35. Zhong, J.-J.; Meng, Q.-Y.; Wang, G.-X.; Liu, Q.; Chen, B.; Feng, K.; Tung, C.-H.; Wu, L.-Z. Chem.-Eur. J. 2013, 19, 6443 10.1002/chem.201204572
36. Wu, C.-J.; Zhong, J.-J.; Meng, Q.-Y.; Lei, T.; Gao, X.-W.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2015, 17 (4) 884 10.1021/ol503744a
37. Wang, B.; Shelar, D. P.; Han, X.-Z.; Li, T.-T.; Guan, X.; Lu, W.; Liu, K.; Chen, Y.; Fu, W.-F.; Che, C.-M. Chem.-Eur. J. 2015, 21, 1184 10.1002/chem.201405356
38. Hari, D. P.; König, B. Org. Lett. 2011, 13, 3852 10.1021/ol201376v
39. Liu, Q.; Li, Y.-N.; Zhang, H.-H.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Chem.-Eur. J. 2012, 18 (2) 620 10.1002/chem.201102299
40. Pan, Y.; Kee, C. W.; Chen, L.; Tan, C.-H. Green Chem. 2011, 13, 2682 10.1039/c1gc15489c
41. Gandy, M. N.; Raston, C. L.; Stubbs, K. A. Chem. Commun. 2015, 51, 11041 10.1039/C5CC02153G
42. Zhao, Y.; Zhang, C.; Chin, K. F.; Pytela, O.; Wei, G.; Liu, H.; Bures, F.; Jiang, Z. RSC Adv. 2014, 4, 30062 10.1039/C4RA05525J
43. Wang, X.-Z.; Meng, Q.-Y.; Zhong, J.-J.; Gao, X.-W.; Lei, T.; Zhao, L.-M.; Li, Z.-J.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Chem. Commun. 2015, 51, 11256 10.1039/C5CC03421C
44. Huang, L.; Zhao, J. RSC Adv. 2013, 3 (45) 23377 10.1039/c3ra43299h
45. Rueping, M.; Vila, C.; Bootwicha, T. ACS Catal. 2013, 3, 1676 10.1021/cs400350j
46. Rueping, M.; Zoller, J.; Fabry, D. C.; Poscharny, K.; Koenigs, R. M.; Weirich, T. E.; Mayer, J. Chem.-Eur. J. 2012, 18, 3478 10.1002/chem.201103242
47. Wang, J.; Ma, J.; Li, X.; Li, Y.; Zhang, G.; Zhang, F.; Fan, X. Chem. Commun. 2014, 50, 14237 10.1039/C4CC06869F
48. Mitkina, T.; Stanglmair, C.; Setzer, W.; Gruber, M.; Kisch, H.; König, B. Org. Biomol. Chem. 2012, 10, 3556 10.1039/c2ob07053g
49. Möhlmann, L.; Baar, M.; Rieß, J.; Antonietti, M.; Wang, X.; Blechert, S. Adv. Synth. Catal. 2012, 354, 1909 10.1002/adsc.201100894
50. Wang, C.; Xie, Z.; DeKrafft, K. E.; Lin, W. J. Am. Chem. Soc. 2011, 133, 13445 10.1021/ja203564w
51. Zhang, W.-Q.; Li, Q.-Y.; Zhang, Q.; Lu, Y.; Lu, H.; Wang, W.; Zhao, X.; Wang, X.-J. Inorg. Chem. 2016, 55, 1005 10.1021/acs.inorgchem.5b02626
52. Xie, Z.; Wang, C.; DeKrafft, K. E.; Lin, W. J. Am. Chem. Soc. 2011, 133, 2056 10.1021/ja109166b
53. Wang, C.; Xie, Z.; DeKrafft, K. E.; Lin, W. ACS Appl. Mater. Interfaces 2012, 4, 2288 10.1021/am3003445
54. Wang, J.-L.; Wang, C.; DeKrafft, K. E.; Lin, W. ACS Catal. 2012, 2, 417 10.1021/cs300027n
55. Jiang, J.-X.; Li, Y.; Wu, X.; Xiao, J.; Adams, D. J.; Cooper, A. I. Macromolecules 2013, 46, 8779 10.1021/ma402104h
56. Xue, Q.; Xie, J.; Jin, H.; Cheng, Y.; Zhu, C. Org. Biomol. Chem. 2013, 11, 1606 10.1039/c3ob27400d
57. Pan, Y.; Wang, S.; Kee, C. W.; Dubuisson, E.; Yang, Y.; Loh, K. P.; Tan, C.-H. Green Chem. 2011, 13, 3341 10.1039/c1gc15865a
58. DeLaive, P. J.; Lee, J. T. T.; Sprintschnik, H. W.; Abruna, H.; Meyer, T. J.; Whitten, D. G. J. Am. Chem. Soc. 1977, 99 (21) 7094 10.1021/ja00463a070
59. DeLaive, P. J.; Foreman, T. K.; Giannotti, C.; Whitten, D. G. J. Am. Chem. Soc. 1980, 102 (1) 5627 10.1021/ja00537a037
60. Zhong, J.-J.; Meng, Q.-Y.; Liu, B.; Li, X.-B.; Gao, X.-W.; Lei, T.; Wu, C.-J.; Li, Z.-J.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2014, 16, 1988 10.1021/ol500534w
61. Zhong, J.-J.; Wu, C.-J.; Meng, Q.-Y.; Gao, X.-W.; Lei, T.; Tung, C.-H.; Wu, L.-Z. Adv. Synth. Catal. 2014, 356, 2846 10.1002/adsc.201400588
62. Further proof for the radical cation is provided by Menche et al. for the Cu-catalyzed CDC reaction: Wang, T.; Schrempp, M.; Berndhäusler, A.; Schiemann, O.; Menche, D. Org. Lett. 2015, 17, 3982 10.1021/acs.orglett.5b01845
63. Nelson, S. F.; Ippoliti, J. T. J. Am. Chem. Soc. 1986, 108, 4879 10.1021/ja00276a028
64. Lewis, F. D. Acc. Chem. Res. 1986, 19, 401 10.1021/ar00132a004
65. Parker, V. D.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 8778 10.1021/ja00023a026
66. Dombrowski, G. W.; Dinnocenzo, J. P.; Zielinski, P. A.; Farid, S.; Wosinska, Z. M.; Gould, I. R. J. Org. Chem. 2005, 70, 3791 10.1021/jo047813g
67. Bock, C. R.; Connor, J. A.; Gutierrez, A. R.; Meyer, T. J.; Whitten, D. G.; Sullivan, B. P.; Nagle, J. K. J. Am. Chem. Soc. 1979, 101 (17) 4815 10.1021/ja00511a007
68. Wayner, D. D. M.; Dannenberg, J. J.; Griller, D. Chem. Phys. Lett. 1986, 131 (3) 189 10.1016/0009-2614(86)80542-5
69. Anderson, C. P.; Salmon, D. J.; Meyer, T. J.; Young, R. C. J. Am. Chem. Soc. 1977, 99 (6) 1980 10.1021/ja00448a054
70. Sawyer, D. T.; Gibian, M. J.; Morrison, M. M.; Seo, E. T. J. Am. Chem. Soc. 1978, 100 (2) 627 10.1021/ja00470a046
71. Xie, J.; Xue, Q.; Jin, H.; Li, H.; Cheng, Y.; Zhu, C. Chem. Sci. 2013, 4, 1281 10.1039/c2sc22131d
72. Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Farès, C.; Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106 10.1021/ja201610c
73. Franz, J. F.; Kraus, W. B.; Zeitler, K. Chem. Commun. 2015, 51, 8280 10.1039/C4CC10270C
74. Xuan, J.; Zeng, T.-T.; Feng, Z.-J.; Deng, Q.-H.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J.; Alper, H. Angew. Chem., Int. Ed. 2015, 54, 1625 10.1002/anie.201409999
75. Ratnikov, M. O.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 1549 10.1021/ja3113559
76. Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Farès, C.; Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106 10.1021/ja201610c
77. Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317 10.1021/ja211697s
78. Boess, E.; Wolf, L. M.; Malakar, S.; Salamone, M.; Bietti, M.; Thiel, W.; Klussmann, M. ACS Catal. 2016, 6, 3253 10.1021/acscatal.6b00944
79. Xia et al. adopted the principle of an off-cycle equilibrium for the photoredox catalyzed Mannich reaction to suppress the formation of amide by-product: Zhao, G.; Yang, C.; Guo, L.; Sun, H.; Chen, C.; Xia, W. Chem. Commun. 2012, 48, 2337 10.1039/c2cc17130a
80. Feldmeier, C.; Bartling, H.; Riedle, E.; Gschwind, R. M. J. Magn. Reson. 2013, 232, 39 10.1016/j.jmr.2013.04.011
81. Lammertsma, K.; Prasad, B. V. J. Am. Chem. Soc. 1993, 115, 2348 10.1021/ja00059a032
82. Lammertsma, K.; Bharatam, P. V. J. Org. Chem. 2000, 65, 4662 10.1021/jo000283d
83. Balamurugan, R.; Manojveer, S. Chem. Commun. 2011, 47 (39) 11143 10.1039/c1cc14926a
84. Engelke, R.; Earl, W. L.; McMichael Rohlfing, C. J. Phys. Chem. 1986, 90 (4) 545 10.1021/j100276a009
85. Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Org. Lett. 2012, 14 (3) 672 10.1021/ol202857t
86. Ruiz Espelt, L.; Wiensch, E. M.; Yoon, T. P. J. Org. Chem. 2013, 78, 4107 10.1021/jo400428m
87. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. J. Am. Chem. Soc. 2012, 134, 3338 10.1021/ja211770y
88. Liu, X.; Ye, X.; Bures, F.; Liu, H.; Jiang, Z. Angew. Chem., Int. Ed. 2015, 54, 11443 10.1002/anie.201505193
89. Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. Heterocycles 1993, 36 (9) 2147 10.3987/COM-93-6436
90. Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 6447 10.1021/jo2011329
91. Bernhard, P.; Sargeson, A. M.; Anson, F. C. Inorg. Chem. 1988, 27, 2754 10.1021/ic00289a003
92. Bernhard, P.; Anson, F. C. Inorg. Chem. 1988, 27 (25) 4574 10.1021/ic00298a014
93. Sawyer, D. T.; Gibian, M. J. Tetrahedron 1979, 35, 1471 10.1016/0040-4020(79)80032-0
94. Wilshire, J.; Sawyer, D. T. Acc. Chem. Res. 1979, 12, 105 10.1021/ar50135a005
95. Nanni, E. J.; Sawyer, D. T. J. Am. Chem. Soc. 1980, 102 (25) 7591 10.1021/ja00545a047
96. Sawyer, D. T.; Valentine, J. S. Acc. Chem. Res. 1981, 14 (12) 393 10.1021/ar00072a005
97. Sawyer, D. T.; Calderwood, T. S.; Johlman, C. L.; Wilkins, C. L. J. Org. Chem. 1985, 50, 1409 10.1021/jo00209a012
98. Zheng, Z.-R.; Kjaer, N. T.; Lund, H. Acta Chem. Scand. 1998, 52, 362 10.3891/acta.chem.scand.52-0362
99. Sawyer, D. T.; Nanni, E. J.; Roberts, J. L. Adv. Chem. Ser. 1982, 201, 585 10.1021/ba-1982-0201.ch024
100. Hayyan, M.; Hashim, M. A.; Alnashef, I. M. Chem. Rev. 2016, 116 (5) 3029 10.1021/acs.chemrev.5b00407
101. Möhlmann, L.; Blechert, S. Adv. Synth. Catal. 2014, 356, 2825 10.1002/adsc.201400551
102. Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 12709 10.1039/c1cc15643h
103. Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105 (15) 5095 10.1021/ja00353a039
104. Tanoue, A.; Yoo, W.-J.; Kobayashi, S. Org. Lett. 2014, 16, 2346 10.1021/ol500661t
105. Ueda, H.; Yoshida, K.; Tokuyama, H. Org. Lett. 2014, 16, 4194 10.1021/ol5018883
106. Rieche, A.; Höft, E.; Schultze, H. Chem. Ber. 1964, 97 (1) 195 10.1002/cber.19640970128
107. Raju, B.; Ragul, R.; Sivasankar, B. N. Indian J. Chem. 2009, 48B, 1315
108. Prieto, F.; Navarro, I.; Rueda, M. J. Phys. Chem. 1996, 100 (96) 16346 10.1021/jp9616472
109. Christie, M. I.; Gillbert, C.; Voisey, M. A. J. Chem. Soc. 1964, 3147 10.1039/jr9640003147
110. Reichel, L. W.; Griffin, G. W.; Muller, A. J.; Das, P. K.; Ege, S. Can. J. Chem. 1984, 62 (3) 424 10.1139/v84-074
111. Lee, L. Y. C.; Ci, X.; Giannotti, C.; Whitten, D. G. J. Am. Chem. Soc. 1986, 108, 175 10.1021/ja00261a029
112. Gaillard, E. R.; Whitten, D. G. Acc. Chem. Res. 1996, 29, 292 10.1021/ar9501885
113. Nagakura, S. Mol. Phys. 1960, 3, 152 10.1080/00268976000100171
114. Gruzdkov, Y. A.; Gupta, Y. M. J. Phys. Chem. A 1998, 102, 2322 10.1021/jp9803236
115. Rived, F.; Rosés, M.; Bosch, E. Anal. Chim. Acta 1998, 374, 309 10.1016/S0003-2670(98)00418-8
116. Muzaffar, S.; Andrabi, A. Indian J. Chem. 2002, 41A, 2306
117. Constantinou, C. P.; Pereira, C.; Chaudhri, M. M. Propellants, Explos., Pyrotech. 1995, 20 (4) 200 10.1002/prep.19950200408
118. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094 10.1021/ja3030164
119. Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426 10.1039/C5SC02185E
120. Megerle, U.; Lechner, R.; König, B.; Riedle, E. Photochem. Photobiol. Sci. 2010, 9, 1400 10.1039/c0pp00195c
121. Klán, P.; Wirz, J. Photochemistry of Organic Compounds: From Concepts to Practice; Wiley-Blackwell, 2009.
122. Riedle, E.; Wenninger, M. In Chemical Photocatalysis; König, B., Ed.; De Gruyter: Berlin, 2013; pp 319-378. Thus, the determination of QYs for different wavelengths of irradiation for the here discussed reaction cannot provide additional information. In order to compare the light-induced reaction at different wavelength and to strengthen the importance of control experiments by variation of the light source, we chose product yields.
123. BHT is a hindered phenol antioxidant, which acts as inhibitor for radical-chain processes. A major pathway of BHT to interrupt radical species is by hydrogen atom transfer, the formed phenoxy radical is relatively unreactive due to steric hindrance by the ortho tert-butyl groups. Yehye, W. A.; Rahman, N. A.; Ariffin, A.; Abd Hamid, S. B.; Alhadi, A. A.; Kadir, F. A.; Yaeghoobi, M. Eur. J. Med. Chem. 2015, 101, 295 10.1016/j.ejmech.2015.06.026
124. Huo, C.; Xie, H.; Wu, M.; Jia, X.; Wang, X.; Chen, F.; Tang, J. Chem.-Eur. J. 2015, 21, 5723 10.1002/chem.201500453
125. Pintér, á.; Sud, A.; Sureshkumar, D.; Klussmann, M. Angew. Chem., Int. Ed. 2010, 49, 5004 10.1002/anie.201000711