Cooperative H2 Activation by Borane-Derived Frustrated Lewis Pairs

Cooperative Catalysis: Designing Efficient Catalysts for Synthesis

Volumn , Issue , 2015, Pages 263-294

  Paradies, Jan ^a  

^a UNIVERSITY OF PADERBORN   (Germany)

Author keywords

Acrylate; Aldimine; Alkylidene malonate; Amine; Asymmetric hydrogenation; Borane; Enamine; Enone; Frustrated Lewis pair; Heterocycle; Hydrogen; Hydrogenation; Ketimine; Lewis acid; Lewis base; Metal free; Nitroolefin; Olefin; Phosphine; Polycyclic aromatic hydrocarbon; Pyridine; Quinoline; Silylenol ether; Small molecule activation; Ynone

Indexed keywords

AMINES; CHEMICAL ACTIVATION; HYDROGEN; OLEFINS; PHOSPHORUS COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS; PYRIDINE; SUBSTRATES;

ACRYLATE; ALDIMINE; ASYMMETRIC HYDROGENATION; BORANE; ENAMINES; ENONE; FRUSTRATED LEWIS PAIRS; HETEROCYCLES; KETIMINES; LEWIS ACID; LEWIS BASE; MALONATES; METAL FREE; NITROOLEFIN; PHOSPHINE; QUINOLINE; SMALL MOLECULE ACTIVATION; YNONE;

HYDROGENATION;

EID: 85015574570     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527681020.ch9     Document Type: Chapter

References (141)

1. Welch, G.C., Juan, R.R.S., Masuda, J.D., and Stephan, D.W. (2006) Science, 314, 11241126.
2. Spies, P., Erker, G., Kehr, G., Bergander, K., Froehlich, R., Grimme, S., and Stephan, D.W. (2007) Chem. Commun., 50725074.
3. Welch, G.C. and Stephan, D.W. (2007) J. Am. Chem. Soc., 129, 18801881.
4. Stephan, D.W. and Erker, G. (2010) Angew Chem., 122, 5081
5. Angew. Chem. Int. Ed., (2010), 49, 4676
6. Erker, G. (2012) Pure Appl. Chem., 84, 22032217
7. Stephan, D.W. (2009) Dalton Trans., 31293136
8. Stephan, D.W. (2008) Org. Biomol. Chem., 6, 15351539
9. Paradies, J. (2013) Synlett, 777780
10. Paradies, J. (2014) Angew. Chem. doi: 10.1002/ange.201309253
11. Angew. Chem. Int. Ed., (2014), doi: 10.1002/anie.201309253.
12. Stephan, D.W. and Erker, G. (2013) Frustrated Lewis Pairs I: Uncovering and Understanding, Vol. 332, Springer, pp. 85110
13. Stephan, D.W. and Erker, G. (2013) Frustrated Lewis Pairs II: Expanding the Scope, Vol. 334, Springer, p. V.
14. Appelt, C., Westenberg, H., Bertini, F., Ehlers, A.W., Slootweg, J.C., Lammertsma, K., and Uhl, W. (2011) Angew. Chem., 123, 40114014
15. Angew. Chem. Int. Ed., (2011), 50, 39253928
16. Appelt, C., Slootweg, J.C., Lammertsma, K., and Uhl, W. (2012) Angew. Chem., 124, 60136016
17. Angew. Chem. Int. Ed., (2012), 51, 59115914
18. Roters, S., Appelt, C., Westenberg, H., Hepp, A., Slootweg, J.C., Lammertsma, K., and Uhl, W. (2012) Dalton Trans., 41, 90339045
19. Westenberg, H., Slootweg, J.C., Hepp, A., Kosters, J., Roters, S., Ehlers, A.W., Lammertsma, K., and Uhl, W. (2010) Organometallics, 29, 13231330
20. Boudreau, J., Courtemanche, M.A., and Fontaine, F.G. (2011) Chem. Commun., 47, 1113111133
21. Menard, G. and Stephan, D.W. (2010) J. Am. Chem. Soc., 132, 17961797
22. Menard, G. and Stephan, D.W. (2011) Angew. Chem., 123, 85468549
23. Angew. Chem. Int. Ed., (2011), 50, 8396-8399
24. Zhang, Y.T., Miyake, G.M., and Chen, E.Y.X. (2010) Angew. Chem., 122, 1035610360
25. Angew. Chem. Int. Ed., (2010), 49, 10158-10162
26. Holtrichter-Rossmann, T., Rosener, C., Hellmann, J., Uhl, W., Wurthwein, E.U., Frohlich, R., and Wibbeling, B. (2012) Organometallics, 31, 32723283. 7.Sgro, M.J. and Stephan, D.W. (2012) Angew. Chem., 124, 1150511507
27. Sgro, M.J. and Stephan, D.W. (2012) Angew. Chem., 124, 1150511507
28. Angew. Chem. Int. Ed., (2012), 51, 1134311345
29. Boone, M.P. and Stephan, D.W. (2013) J. Am. Chem. Soc., 135, 85088511
30. Boone, M.P. and Stephan, D.W. (2014) Chem. Eur. J. doi: 10.1002/chem.201304289.
31. Chapman, A.M., Haddow, M.F., and Wass, D.F. (2011) J. Am. Chem. Soc., 133, 1846318478
32. Chapman, A.M., Haddow, M.F., and Wass, D.F. (2011) J. Am. Chem. Soc., 133, 88268829
33. Wass, D.F. and Chapman, A.M. (2013) Frustrated Lewis Pairs II: Expanding the Scope, Vol. 334, Springer, pp. 261280
34. Chapman, A.M., Haddow, M.F., and Wass, D.F. (2012) Eur. J. Inorg. Chem., 9, 15461554
35. Chapman, A.M. and Wass, D.F. (2012) Dalton Trans., 41, 90679072
36. Khan, S. and Alcarazo, M. (2013) Frustrated Lewis Pairs II: Expanding the Scope, Vol. 334, Springer, pp. 157170.
37. Alcarazo, M., Gomez, C., Holle, S., and Goddard, R. (2010) Angew. Chem., 122, 59245927
38. Angew. Chem. Int. Ed., (2010), 49, 57885791
39. Cabrera, L., Welch, G.C., Masuda, J.D., Wei, P.R., and Stephan, D.W. (2006) Inorg. Chim. Acta, 359, 30663071
40. Schafer, A., Reissmann, M., Schafer, A., Saak, W., Haase, D., and Muller, T. (2011) Angew. Chem., 123, 1284512848
41. Angew. Chem. Int. Ed., (2011), 50, 1263612638.
42. Brown, H.C., Schlesinger, H.I., and Cardon, S.Z. (1942) J. Am. Chem. Soc., 64, 325333.
43. Rokob, T.A., Hamza, A., Stirling, A., Soos, T., and Papai, I. (2008) Angew. Chem., 120, 24692472
44. Angew. Chem. Int. Ed., (2008), 47, 24352438
45. Hamza, A., Stirling, A., Rokob, T.A., and Papai, I. (2009) Int. J. Quantum Chem., 109, 24162425
46. Rokob, T.A., Bako, I., Stirling, A., Hamza, A., and Papai, I. (2013) J. Am. Chem. Soc., 135, 44254437
47. Rokob, T.A., Hamza, A., Stirling, A., and Papai, I. (2009) J. Am. Chem. Soc., 131, 20292036
48. Grimme, S., Kruse, H., Goerigk, L., and Erker, G. (2010) Angew. Chem., 122, 14441447
49. Angew. Chem. Int. Ed., (2010), 49, 14021405
50. Momming, C.M., Fromel, S., Kehr, G., Frohlich, R., Grimme, S., and Erker, G. (2009) J. Am. Chem. Soc., 131, 1228012289
51. Mmming, C.M., Otten, E., Kehr, G., Frhlich, R., Grimme, S., Stephan, D.W., and Erker, G. (2009) Angew. Chem., 121, 67706773
52. Angew. Chem. Int. Ed., (2009), 48, 66436646.
53. Rocchigiani, L., Ciancaleoni, G., Zuccaccia, C., and Macchioni, A. (2014) J. Am. Chem. Soc., 136, 112115.
54. Schirmer, B. and Grimme, S. (2010) Chem. Commun., 46, 79427944.
55. Rokob, T.A., Hamza, A., and Papai, I. (2009) J. Am. Chem. Soc., 131, 1070110710.
56. Spies, P., Schwendemann, S., Lange, S., Kehr, G., Frhlich, R., and Erker, G. (2008) Angew. Chem., 120, 76547657
57. Angew. Chem. Int. Ed., (2008), 47, 75437546.
58. Wang, H.D., Frhlich, R., Kehr, G., and Erker, G. (2008) Chem. Commun., 59665968
59. Greb, L., Ona-Burgos, P., Kubas, A., Falk, F.C., Breher, F., Fink, K., and Paradies, J. (2012) Dalton Trans., 41, 90569060.
60. Jiang, C. and Stephan, D.W. (2013) Dalton Trans., 42, 630637.
61. Stephan, D.W., Greenberg, S., Graham, T.W., Chase, P., Hastie, J.J., Geier, S.J., Farrell, J.M., Brown, C.C., Heiden, Z.M., Welch, G.C., and Ullrich, M. (2011) Inorg. Chem., 50, 1233812348. 19.Sumerin, V., Schulz, F., Atsumi, M., Wang, C., Nieger, M., Leskela, M., Repo, T., Pyykko, P., and Rieger, B. (2008) J. Am. Chem. Soc., 130, 1411714118
62. Sumerin, V., Schulz, F., Atsumi, M., Wang, C., Nieger, M., Leskela, M., Repo, T., Pyykko, P., and Rieger, B. (2008) J. Am. Chem. Soc., 130, 1411714118
63. Sumerin, V., Schulz, F., Nieger, M., Leskela, M., Repo, T., and Rieger, B. (2008) Angew. Chem., 120, 60906092
64. Angew. Chem. Int. Ed., (2008), 47, 60016003.
65. Hounjet, L.J., Bannwarth, C., Garon, C.N., Caputo, C.B., Grimme, S., and Stephan, D.W. (2013) Angew. Chem., 125, 76407643
66. Angew. Chem. Int. Ed., (2013), 52, 74927495.
67. Frey, G.D., Lavallo, V., Donnadieu, B., Schoeller, W.W., and Bertrand, G. (2007) Science, 316, 439441
68. Chase, P.A. and Stephan, D.W. (2008) Angew. Chem., 120, 75437547
69. Angew. Chem. Int. Ed., (2008), 47, 74337437
70. Holschumacher, D., Bannenberg, T., Hrib, C.G., Jones, P.G., and Tamm, M. (2008) Angew. Chem., 120, 75387542
71. Angew. Chem. Int. Ed., (2008), 47, 74287432
72. Chase, P.A., Gille, A.L., Gilbert, T.M., and Stephan, D.W. (2009) Dalton Trans., 71797188
73. Holschumacher, D., Taouss, C., Bannenberg, T., Hrib, C.G., Daniliuc, C.G., Jones, P.G., and Tamm, M. (2009) Dalton Trans., 69276929
74. Holschumacher, D., Daniliuc, C.G., Jones, P.G., and Tamm, M. (2011) Z. Naturforsch., B Chem. Sci., 66, 371377
75. Kronig, S., Theuergarten, E., Holschumacher, D., Bannenberg, T., Daniliuc, C.G., Jones, P.G., and Tamm, M. (2011) Inorg. Chem., 50, 73447359.
76. Li, H., Aquino, A.J.A., Cordes, D.B., Hung-Low, F., Hase, W.L., and Krempner, C. (2013) J. Am. Chem. Soc., 135, 1606616069
77. Periasamy, M. and Thirumalaikumar, P. (2000) J. Organomet. Chem., 609, 137151
78. Seyden-Penne, J. (1991) Reductions by the Alumino- and Borohydrides in Organic Synthesis, VCH-Lavoisier, Paris.
79. Chase, P.A., Welch, G.C., Jurca, T., and Stephan, D.W. (2007) Angew. Chem., 119, 81968199
80. Angew. Chem. Int. Ed., (2007), 46, 80508053.
81. Chase, P.A., Jurca, T., and Stephan, D.W. (2008) Chem. Commun., 17011703.
82. Greb, L., Tussing, S., Schirmer, B., Ona-Burgos, P., Kaupmees, K., Lokov, M., Leito, I., Grimme, S., and Paradies, J. (2013) Chem. Sci., 4, 27882796
83. Greb, L., Ona-Burgos, P., Schirmer, B., Grimme, S., Stephan, D.W., and Paradies, J. (2012) Angew. Chem., 124, 1031110315
84. Angew. Chem. Int. Ed., (2012), 51, 1016410168.
85. Beckett, M.A., Brassington, D.S., Coles, S.J., and Hursthouse, M.B. (2000) Inorg. Chem. Commun., 3, 530533
86. Beckett, M.A., Strickland, G.C., Holland, J.R., and Sukumar Varma, K. (1996) Polymer, 37, 46294631
87. Gutmann, V. (1976) Coord. Chem. Rev., 18, 225255
88. Mayer, U., Gutmann, V., and Gerger, W. (1975) Monatsh. Chem., 106, 12351257.
89. Childs, R.F., Mulholland, D.L., and Nixon, A. (1982) Can. J. Chem., 60, 801808.
90. Ullrich, M., Lough, A.J., and Stephan, D.W. (2009) J. Am. Chem. Soc., 131, 5253.
91. Nicasio, J.A., Steinberg, S., Ines, B., and Alcarazo, M. (2013) Chem. Eur. J., 19, 1101611020.
92. Greb, L., Daniliuc, C.G., Bergander, K., and Paradies, J. (2013) Angew. Chem., 125, 59895992
93. Angew. Chem. Int. Ed., (2013), 52, 58765879.
94. Eros, G., Mehdi, H., Papai, I., Rokob, T.A., Kiraly, P., Tarkanyi, G., and Sos, T. (2010) Angew. Chem., 122, 67096713
95. Angew. Chem. Int. Ed., (2010), 49, 65596563.
96. Greb, L. and Paradies, J. (2013) Frustrated Lewis Pairs II: Expanding the Scope, Vol. 334, Springer, pp. 81100.
97. Binding, S.C., Zaher, H., Mark Chadwick, F., and OHare, D. (2012) Dalton Trans., 41, 90619066.
98. Lu, Z.P., Cheng, Z.H., Chen, Z.X., Weng, L.H., Li, Z.H., and Wang, H.D. (2011) Angew. Chem., 123, 1243512439
99. Angew. Chem. Int. Ed., (2011), 50, 1222712231.
100. Herrington, T.J., Thom, A.J.W., White, A.J.P., and Ashley, A.E. (2012) Dalton Trans., 41, 90199022.
101. Eros, G., Nagy, K., Mehdi, H., Papai, I., Nagy, P., Kiraly, P., Tarkanyi, G., and Sos, T. (2012) Chem. Eur. J., 18, 574585
102. Sos, T. (2011) Pure Appl. Chem., 83, 667675.
103. Ins, B., Palomas, D., Holle, S., Steinberg, S., Nicasio, J.A., and Alcarazo, M. (2012) Angew. Chem., 124, 1253312536
104. Angew. Chem. Int. Ed., (2012), 51, 1236712369.
105. Parks, D.J., Spence, R.E.V.H., and Piers, W.E. (1995) Angew. Chem., 107, 895897
106. Angew. Chem. Int. Ed., (1995), 34, 809811
107. Parks, D.J. and Piers, W.E. (1998) Tetrahedron, 54, 1546915488
108. Parks, D.J., Piers, W.E., and Yap, G.P.A. (1998) Organometallics, 17, 54925503.
109. Schwendemann, S., Tumay, T.A., Axenov, K.V., Peuser, I., Kehr, G., Frohlich, R., and Erker, G. (2010) Organometallics, 29, 10671069.
110. Axenov, K.V., Momming, C.M., Kehr, G., Frohlich, R., and Erker, G. (2010) Chem. Eur. J., 16, 1406914073.
111. Schwendemann, S., Frhlich, R., Kehr, G., and Erker, G. (2011) Chem. Sci., 2, 18421849.
112. Sumerin, V., Chernichenko, K., Nieger, M., Leskela, M., Rieger, B., and Repo, T. (2011) Adv. Synth. Catal., 353, 20932110
113. Chernichenko, K., Nieger, M., Leskela, M., and Repo, T. (2012) Dalton Trans., 41, 90299032.
114. Chernichenko, K., Madarasz, A., Papai, I., Nieger, M., Leskela, M., and Repo, T. (2013) Nat. Chem., 5, 718723.
115. Stute, A., Kehr, G., Frhlich, R., and Erker, G. (2011) Chem. Commun., 47, 42884290
116. Stute, A., Heletta, L., Frohlich, R., Daniliuc, C.G., Kehr, G., and Erker, G. (2012) Chem. Commun., 48, 1173911741.
117. Stute, A., Kehr, G., Daniliuc, C.G., Frohlich, R., and Erker, G. (2013) Dalton Trans., 42, 44874499
118. Sajid, M., Lawzer, A., Dong, W.S., Rosorius, C., Sander, W., Schirmer, B., Grimme, S., Daniliuc, C.G., Kehr, G., and Erker, G. (2013) J. Am. Chem. Soc., 135, 1856718574
119. Rosorius, C., Daniliuc, C.G., Frohlich, R., Kehr, G., and Erker, G. (2013) J. Organomet. Chem., 744, 149155
120. Ekkert, O., Miera, G.G., Wiegand, T., Eckert, H., Schirmer, B., Petersen, J.L., Daniliuc, C.G., Frhlich, R., Grimme, S., Kehr, G., and Erker, G. (2013) Chem. Sci., 4, 26572664
121. Rosorius, C., Kehr, G., Frhlich, R., Grimme, S., and Erker, G. (2011) Organometallics, 30, 42114219.
122. Chen, D.J., Wang, Y.T., and Klankermayer, J. (2010) Angew. Chem., 122, 96659668
123. Angew. Chem. Int. Ed., (2010), 49, 94759478
124. Chen, D.J., Leich, V., Pan, F.F., and Klankermayer, J. (2012) Chem. Eur. J., 18, 51845187;
125. Chen, D.J. and Klankermayer, J. (2008) Chem. Commun., 21302131
126. Ghattas, G., Chen, D.J., Pan, F.F., and Klankermayer, J. (2012) Dalton Trans., 41, 90269028.
127. Liu, Y.B. and Du, H.F. (2013) J. Am. Chem. Soc., 135, 68106813.
128. Erker, G. and Stephan, D.W. (2013) in Topics in Current Chemistry: Frustrated Lewis Pairs, Vol. 1 (ed. D.W.S. Gerhard Erker), Springer-Verlag, Berlin, Heidelberg, pp. 85110. 50.Pellissier, H. (2013) Chem. Rev., 113, 442524
129. Tietze, L.F. (1996) Chem. Rev., 96, 115136.
130. Blackwell, J.M., Morrison, D.J., and Piers, W.E. (2002) Tetrahedron, 58, 82478254.
131. Geier, S.J., Chase, P.A., and Stephan, D.W. (2010) Chem. Commun., 46, 48844886.
132. Mahdi, T., del Castillo, J.N., and Stephan, D.W. (2013) Organometallics, 32, 19711978.
133. Liu, Y. and Du, H. (2013) J. Am. Chem. Soc., 135, 1296812971.
134. Reddy, J.S., Xu, B.-H., Mahdi, T., Frhlich, R., Kehr, G., Stephan, D.W., and Erker, G. (2012) Organometallics, 31, 56385649
135. Xu, B.H., Kehr, G., Frhlich, R., Wibbeling, B., Schirmer, B., Grimme, S., and Erker, G. (2011) Angew. Chem., 132, 73217324
136. Angew. Chem. Int. Ed., (2011), 50, 7183-7186.
137. Segawa, Y. and Stephan, D.W. (2012) Chem. Commun., 48, 1196311965
138. Dewitt, E.J., Trapasso, L.E., and Ramp, F.L. (1961) J. Am. Chem. Soc., 83, 4672
139. Ramp, F.L., Dewitt, E.J., and Trapasso, L.E. (1962) J. Org. Chem., 27, 43684372.
140. Wang, Y., Chen, W., Lu, Z., Li, Z.H., and Wang, H. (2013) Angew. Chem., 125, 76447647
141. Angew. Chem. Int. Ed., (2013), 52, 74967499.