Catalytic hydrogenation with frustrated lewis pairs: Selectivity achieved by size-exclusion design of lewis acids

Chemistry - A European Journal

Volumn 18, Issue 2, 2012, Pages 574-585

  Erös, Gábor ^a   Nagy, Krisztina ^a   Mehdi, Hasan ^a   Pápai, Imre ^a   Nagy, Péter ^a   Király, Péter ^a   Tárkányi, Gábor ^a   Soõs, Tibor ^a  

^a CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

chemoselectivity; hydrogenation; Lewis acids; Lewis bases; size exclusion

Indexed keywords

CATALYST DESIGNS; CATALYTIC HYDROGENATION; CHEMO-SELECTIVITY; CHEMOSELECTIVE REDUCTION; HYDROGEN MOLECULE; ISOTOPIC LABELING; LEWIS ACID; LEWIS BASIS; PHYSICAL CONSTRAINTS; SIZE EXCLUSION; UNSATURATED IMINES;

BORON; BORON COMPOUNDS; CATALYST SELECTIVITY; HYDROGEN; KETONES; REDUCTION; TRANSITION METALS;

HYDROGENATION;

BORANE DERIVATIVE; LEWIS ACID; QUINOLINE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION;

BORANES; CATALYSIS; HYDROGENATION; LEWIS ACIDS; MODELS, MOLECULAR; OXIDATION-REDUCTION; QUINOLINES;

EID: 84855327166     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102438     Document Type: Article

References (109)

1. Pioneering work
2. G. C. Welch, R. R. San Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124-1126. Most recent review on FLP chemistry
3. D. W. Stephan, G. Erker, Angew. Chem. 2010, 122, 50-81
4. 2 splitting
5. J. H. Teles, S. Brode, A. Berkessel, J. Am. Chem. Soc. 1998, 120, 1345-1346
6. A. Berkessel, T. J. S. Schubert, T. N. Müller, J. Am. Chem. Soc. 2002, 124, 8693-8698
7. R. Roesler, W. E. Piers, M. Parvez, J. Organomet. Chem. 2003, 680, 218-222.
8. T. A. Rokob, A. Hamza, A. Stirling, T. Soõs, I. Pápai, Angew. Chem. 2008, 120, 2469-2472
9. Angew. Chem. Int. Ed. 2008, 47, 2435-2438.
10. Y. Guo, S. Li, Eur. J. Inorg. Chem. 2008, 2501-2505
11. A. Stirling, A. Hamza, T. A. Rokob, I. Pápai, Chem. Commun. 2008, 3148-3150
12. Y. Guo, S. Li, Inorg. Chem. 2008, 47, 6212-6219
13. T. Privalov, Chem. Eur. J. 2009, 15, 1825-1829
14. T. Privalov, Dalton Trans. 2009, 1321-1327
15. T. A. Rokob, A. Hamza, A. Stirling, I. Pápai, J. Am. Chem. Soc. 2009, 131, 2029-2036
16. T. Privalov, Eur. J. Inorg. Chem. 2009, 2229-2237
17. A. Hamza, A. Stirling, T. A. Rokob, I. Pápai, Int. J. Quantum Chem. 2009, 109, 2416-2425
18. J. Nyhlén, T. Privalov, Eur. J. Inorg. Chem. 2009, 2759-2764
19. T. A. Rokob, A. Hamza, I. Pápai, J. Am. Chem. Soc. 2009, 131, 10701-10710
20. S. Gao, W. Wu, Y. Mo, J. Phys. Chem. A 2009, 113, 8108-8117
21. J. Nyhlén, T. Privalov, Dalton Trans. 2009, 5780-5786
22. H. W. Kim, Y. M. Rhee, Chem. Eur. J. 2009, 15, 13348-13355
23. R. Rajeev, R. B. Sunoj, Chem. Eur. J. 2009, 15, 12846-12855
24. S. Grimme, H. Kruse, L. Goerigk, G. Erker, Angew. Chem. 2010, 122, 1444-1447
25. Angew. Chem. Int. Ed. 2010, 49, 1402-1405
26. G. Lu, H. Li, L. Zhao, F. Huang, Z. Wang, Inorg Chem. 2010, 49, 295-301
27. W. E. Piers, A. J. V. Marwitz, L. G. Mercier, Inorg. Chem. 2011, DOI:.
28. G. C. Welch, D. W. Stephan, J. Am. Chem. Soc. 2007, 129, 1880-1881
29. P. Spies, G. Erker, G. Kehr, K. Bergander, R. Fröhlich, S. Grimme, D. W. Stephan, Chem. Commun. 2007, 5072-5074
30. S. J. Geier, T. M. Gilbert, D. W. Stephan, J. Am. Chem. Soc. 2008, 130, 12632-12633
31. D. P. Huber, G. Kehr, K. Bergander, R. Fröhlich, G. Erker, S. Tanino, Y. Ohki,;, K. Tatsumi, Organometallics 2008, 27, 5279-5284
32. H. Wang, R. Fröhlich, G. Kehr, G. Erker, Chem. Commun. 2008, 5966-5968
33. M. Ullrich, A. J. Lough, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 52-53
34. A. Ramos, A. J. Lough, D. W. Stephan, Chem. Commun. 2009, 1118-1120
35. P. Spies, G. Kehr, K. Bergander, B. Wibbeling, R. Fröhlich, G. Erker, Dalton Trans. 2009, 1534-1541
36. C. Jiang, O. Blacque, H. Berke, Organometallics 2009, 28, 5233-5239.
37. P. A. Chase, T. Jurca, D. W. Stephan, Chem. Commun. 2008, 1701-1703
38. D. Chen, J. Klankermayer, Chem. Commun. 2008, 2130-2131
39. V. Sumerin, F. Schulz, M. Nieger, M. Leskelä, T. Repo, B. Rieger, Angew. Chem. 2008, 120, 6090-6092
40. Angew. Chem. Int. Ed. 2008, 47, 5861-5863
41. V. Sumerin, F. Schulz, M. Atsumi, C. Wang, M. Nieger, M. Leskelä, T. Repo, P. Pyykkö, B. Rieger, J. Am. Chem. Soc. 2008, 130, 14117-14119
42. K. V. Axenov, G. Kehr, R. Fröhlich, G. Erker, J. Am. Chem. Soc. 2009, 131, 3454-3455
43. S. J. Geier, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 3476-3477
44. V. Sumerin, F. Schulz, M. Nieger, M. Atsumi, C. Wang, M. Leskelä, P. Pyykkö, T. Repo, B. Rieger, J. Organomet. Chem. 2009, 694, 2654-2660
45. C. Jiang, O. Blacque, H. Berke, Chem. Commun. 2009, 5518-5520
46. E. Theuergarten, D. Schlüns, J. Grunenberg, C. G. Daniliuc, P. G. Jones, M. Tamm, Chem. Commun. 2010, 46, 8561-8563
47. C. Jiang, O. Blacque, T. Fox, H. Berke, Organometallics 2011, 30, 2117-2124.
48. D. Holschumacher, T. Bannenberg, C. G. Hrib, P. G. Jones, M. Tamm, Angew. Chem. 2008, 120, 7538-7542
49. Angew. Chem. Int. Ed. 2008, 47, 7428-7432
50. P. A. Chase, D. W. Stephan, Angew. Chem. 2008, 120, 7543-7547
51. Angew. Chem. Int. Ed. 2008, 47, 7433-7437
52. P. A. Chase, A. L. Gille, T. M. Gilbert, D. W. Stephan, Dalton Trans. 2009, 7179-7188.
53. P. A. Chase, G. C Welch, T. Jurca, D. W. Stephan, Angew. Chem. 2007, 119, 8196-8199
54. Angew. Chem. Int. Ed. 2007, 46, 8050-8053. Recent review
55. D. W. Stephan, S. Greenberg, T. W. Graham, P. Chase, J. J. Hastie, S. J. Geier, J. M. Farrell, C. C. Brown, Z. M. Heiden, G. C. Welch, M. Ullrich, Inorg. Chem., DOI:.
56. Z. M. Heiden, D. W. Stephan, Chem. Commun. 2011, 47, 5729-5731; see References [4a], [4d], [4e], [4g], [5a-c], [5e], [5f-h], [6a-c].
57. D. Chen, Y. Wang, J. Klankermayer, Angew. Chem. 2010, 122, 9665-9668
58. Angew. Chem. Int. Ed. 2010, 49, 9475-9478.
59. C. M. Mömming, S. Frömel, G. Kehr, R. Fröhlich, S. Grimme, G. Erker, J. Am. Chem. Soc. 2009, 131, 12280-12289.
60. M. Ullrich, K. S.-H. Seto, A. J. Lough, D. W. Stephan, Chem. Commun. 2009, 2335-2337.
61. M. A. Dureen, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 8396-8397
62. C. Appelt, H. Westenberg, F. Bertini, A. W. Ehlers, J. C. Slootweg, K. Lammertsma, W. Uhl, Angew. Chem. Int. Ed. 2011, 50, 3925-3928.
63. G. M. Morton, M. A. Dureen, D. W. Stephan, Chem. Commun. 2010, 46, 8947-8949.
64. S. Moebs-Sanchez, G. Bouhadir, N. Saffon, L. Maron, D. Bourissou, Chem. Commun. 2008, 3435-3437.
65. E. Otten, R. C. Neu, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 9918-9919.
66. C. M. Mömming, E. Otten, G. Kehr, R. Fröhlich, S. Grimme, D. W. Stephan, G. Erker, Angew. Chem. 2009, 121, 6770-6773
67. Angew. Chem. Int. Ed. 2009, 48, 6643-6646.
68. S. Porcel, G. Bouhadir, N. Saffon, L. Maron, D. Bourissou, Angew. Chem. 2010, 122, 6322-6325
69. Angew. Chem. Int. Ed. 2010, 49, 6186-6189.
70. G. Erös, H. Mehdi, I. Pápai, T. A. Rokob, P. Király, G. Tárkányi, T. Soõs, Angew. Chem. 2010, 122, 6709-6713
71. Angew. Chem. Int. Ed. 2010, 49, 6559-6563
72. recent review of our work:, T. Soõs, Pure Appl. Chem. 2011, 83, 667-675.
73. P. B. Weisz, Pure Appl. Chem. 1980, 52, 2091-2103.
74. H. Zheng, J. D. Lipscomb, Biochemistry 2006, 45, 1685-1692.
75. A comprehensive review on 1,2,3,4-tetrahydroquinolines:, A. R. Katritzky, S. Rachwal, B. Rachwal, Tetrahedron 1996, 52, 15031-15070.
76. R. H. Fish, J. L. Tan, A. D. Thormodsen, Organometallics 1985, 4, 1743-1747
77. R. T. Shuman, P. L. Omstein, J. W. Paschal, P. D. Gesellchen, J. Org. Chem. 1990, 55, 738-741
78. E. Baralt, S. J. Smith, J. Hurwitz, I. T. Horváth, R. H. Fish, J. Am. Chem. Soc. 1992, 114, 5187-5196
79. W.-B. Wang, S.-M. Lu, P.-Y. Yang, X.-W. Han, Y.-G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536-10537
80. N. MršiÄ, L. Lefort, J. A. F. Boogers, A. J. Minnaard, B. L. Feringa, J. G. de Vries, Adv. Synth. Catal. 2008, 350, 1081-1089
81. R. Yamaguchi, C. Ikeda, Y. Takahashi, K.-I. Fujita, J. Am. Chem. Soc. 2009, 131, 8410-8412.
82. B. E. Maryanoff, D. F. McComsey, S. O. Nortey, J. Org. Chem. 1981, 46, 355-360
83. B. S. Rauckman, M. Y. Tidwell, J. V. Johnson, B. J. Roth, J. Med. Chem. 1989, 32, 1927-1935
84. A. Srikrishna, T. J. Reddy, R. Viswajanani, Tetrahedron 1996, 52, 1631-1636.
85. Employing alkali metals:, P. Nandi, J. L. Dye, J. E. Jackson, J. Org. Chem. 2009, 74, 5790-5792.
86. M. Rueping, T. Theissmann, A. P. Antonchick, Synlett 2006, 1071-1074
87. M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765-3768
88. Angew. Chem. Int. Ed. 2006, 45, 3683-3686
89. M. Rueping, T. Theissmann, S. Raja, J. W. Bats, Adv. Synth. Catal. 2008, 350, 1001-1006
90. M. Rueping, T. Theissmann, Chem. Sci. 2010, 1, 473-476.
91. D.-W. Wang, D.-S. Wang, Q.-A. Chen, Y.-G. Zhou, Chem. Eur. J. 2010, 16, 1133-1136.
92. S. J. Geier, P. A. Chase, D. W. Stephan, Chem. Commun. 2010, 46, 4884-4886.
93. At elevated temperature, a nucleophilic aromatic substitution might occur at the para position on a pentafluorophenyl ring. See, for example:, G. C. Welch, R. Prieto, M. A. Dureen, A. J. Lough, O. A. Labeodan, T. Höltrichter-Rössmanna, D. W. Stephan, Dalton Trans. 2009, 1559-1570.
94. H. E. Podall, H. E. Petree, J. R. Zietz, J. Org. Chem. 1959, 24, 1222-1226
95. R. Köster, G. Bruno, P. Binger, Justus Liebigs Ann. Chem. 1961, 644, 1-22
96. E. J. DeWitt, F. L. Ramp, L. E. Trapasso, J. Am. Chem. Soc. 1961, 83, 4672.
97. A. O'Byrne, P. Evans, Tetrahedron 2008, 64, 8067-8072
98. B. L. Chen, B. Wang, G. Q. Lin, J. Org. Chem. 2010, 75, 941-944
99. H. Nöth, B. Wrackmeyer, Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, Springer, Berlin, 1978.
100. Systematic variation of the steric bulk of pyridine derivatives 1 a could lead to the balanced population:, S. J. Geier, A. L. Gille, T. M. Gilbert, D. W. Stephan, Inorg. Chem. 2009, 48, 10466-10474.
101. P. R. Rinaldi, J. Am. Chem. Soc. 1983, 105, 5167-5168
102. J.-P. Macheteau, H. Oulyadi, B. van Hemelryck, M. Bourdonneau, D. Davoust, J. Fluorine Chem. 2000, 104, 149-154
103. J. Battiste, R. A. Prog. Newmark, Prog. Nucl. Magn. Reson. Spectrosc. 2006, 48, 1-23
104. T. Beringhelli, G. D′Alfonso, D. Donghi, D. Maggioni, P. Mercandelli, A. Sironi, Organometallics 2007, 26, 2088-2095.
105. 4;, R. C. Elderfield, B. H. Wark, J. Org. Chem. 1962, 27, 543-548.
106. E. A. Braude, J. Hannah, R. Linstead, J. Chem. Soc. 1960, 3249-3257
107. D. E. Minter, P. L. Stotter, J. Org. Chem. 1981, 46, 3965-3970
108. T. P. Forrest, G. A. Dauphinee, S. A. Deraniyagala, Can. J. Chem. 1985, 63, 412-415
109. N. S. Mani, P. Chen, T. K. Jones, J. Org. Chem. 1999, 64, 6911-6914.