Nonheme iron-mediated amination of C(sp3)-H bonds. Quinquepyridine-supported iron-imide/nitrene intermediates by experimental studies and DFT calculations

Journal of the American Chemical Society

Volumn 135, Issue 19, 2013, Pages 7194-7204

  Liu, Yungen ^a   Guan, Xiangguo ^a   Wong, Ella Lai Ming ^a   Liu, Peng ^a   Huang, Jie Sheng ^a   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION REACTION; C-H BOND DISSOCIATION ENERGY; CROSSOVER EXPERIMENTS; EXPERIMENTAL STUDIES; H-ATOM ABSTRACTION; NITROGEN SOURCES; REACTION BARRIERS; REACTION MIXTURE;

AMINES; DENSITY FUNCTIONAL THEORY; GROUND STATE; IRON; PARAFFINS; REACTION INTERMEDIATES;

IRON COMPOUNDS;

ALKANE; ANDROSTANE DERIVATIVE; CARBON; CHOLANE DERIVATIVE; CYCLOALKANE; CYCLOHEXANE; ESTER; HYDROCARBON; HYDROGEN; NITROGEN; PYRIDINE; QUINQUEPYRIDINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYST; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND;

EID: 84877829179     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3122526     Document Type: Article

References (162)

1. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
2. Zalatan, D. N.; Du Bois, J. In C-H Activation; Yu, J.-Q.; Shi, Z., Eds.; Springer-Verlag: Berlin, 2010; p 347.
3. Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926
4. Che, C.-M.; Lo, V. K.-Y.; Zhou, C.-Y.; Huang, J.-S. Chem. Soc. Rev. 2011, 40, 1950
5. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
6. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217
7. Bauer, E. B. Curr. Org. Chem. 2008, 12, 1341
8. Correa, A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108
9. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317
10. Iron Catalysis: Fundamentals and Applications; Plietker, B., Ed.; Springer-Verlag: Berlin, 2011.
11. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841
12. Ortiz de Montellano, P. R. Chem. Rev. 2010, 110, 932
13. Lewis, J. C.; Coelho, P. S.; Arnold, F. H. Chem. Soc. Rev. 2011, 40, 2003
14. Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759
15. Kopp, D. A.; Lippard, S. J. Curr. Opin. Chem. Biol. 2002, 6, 568
16. Baik, M.-H.; Newcomb, M.; Friesner, R. A.; Lippard, S. J. Chem. Rev. 2003, 103, 2385
17. Costas, M.; Chen, K.; Que, L., Jr. Coord. Chem. Rev. 2000, 200-202, 517
18. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L., Jr. Chem. Rev. 2004, 104, 939
19. Lippard, S. J. Philos. Trans. R. Soc., A 2005, 363, 861
20. Kryatov, S. V.; Rybak-Akimova, E. V.; Schindler, S. Chem. Rev. 2005, 105, 2175
21. Que, L., Jr.; Tolman, W. B. Nature 2008, 455, 333
22. White, M. C. Science 2012, 335, 807
23. Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728
24. Wang, Z.; Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2008, 10, 1863
25. Liu, P.; Wong, E. L.-M.; Yuen, A. W.-H.; Che, C.-M. Org. Lett. 2008, 10, 3275
26. King, E. R.; Hennessy, E. T.; Betley, T. A. J. Am. Chem. Soc. 2011, 133, 4917
27. For a review on catalysis involving iron imide/nitrene intermediates, see: Che, C.-M.; Zhou, C.-Y.; Wong, E. L.-M. In Iron Catalysis: Fundamentals and Applications; Plietker, B., Ed.; Springer-Verlag: Berlin, 2011; p 111.
28. Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015
29. Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033
30. Bach, T.; Körber, C. J. Org. Chem. 2000, 65, 2358
31. Katsuki, T. Chem. Lett. 2005, 34, 1304
32. García Mancheño, O.; Bolm, C. Org. Lett. 2006, 8, 2349
33. García Mancheño, O.; Dallimore, J.; Plant, A.; Bolm, C. Org. Lett. 2009, 11, 2429
34. Simkhovich, L.; Gross, Z. Tetrahedron Lett. 2001, 42, 8089
35. Heuss, B. D.; Mayer, M. F.; Dennis, S.; Hossain, M. M. Inorg. Chim. Acta 2003, 342, 301
36. Avenier, F.; Latour, J.-M. Chem. Commun. 2004, 1544
37. Klotz, K. L.; Slominski, L. M.; Hull, A. V.; Gottsacker, V. M.; Mas-Ballesté, R.; Que, L., Jr.; Halfen, J. A. Chem. Commun. 2007, 2063
38. Mayer, A. C.; Salit, A.-F.; Bolm, C. Chem. Commun. 2008, 5975
39. Nakanishi, M.; Salit, A. F.; Bolm, C. Adv. Synth. Catal. 2008, 350, 1835
40. Klotz, K. L.; Slominski, L. M.; Riemer, M. E.; Phillips, J. A.; Halfen, J. A. Inorg. Chem. 2009, 48, 801
41. Cramer, S. A.; Jenkins, D. M. J. Am. Chem. Soc. 2011, 133, 19342
42. Nonheme iron-catalyzed hydrogenation of azides: Bart, S. C.; Lobkovsky, E.; Bill, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 5302
43. Nonheme iron-catalyzed formation of carbodiimides or isocyanates from organic azides and isocyanides or CO: Cowley, R. E.; Eckert, N. A.; Elhaïk, J.; Holland, P. L. Chem. Commun. 2009, 1760
44. Nonheme iron-catalyzed N-N coupling of aryl azides to azoarenes Mankad, N. P.; Müller, P.; Peters, J. C. J. Am. Chem. Soc. 2010, 132, 4083
45. Chen, G.-Q.; Xu, Z.-J.; Liu, Y.; Zhou, C.-Y.; Che, C.-M. Synlett 2011, 1174
46. Ton, T. M. U.; Tejo, C.; Tania, S.; Chang, J. W. W.; Chan, P. W. H. J. Org. Chem. 2011, 76, 4894
47. 2 (∼4 equiv) + chloroamine-T (∼4 equiv)" was reported; the reaction was proposed to proceed via initial chlorination of adamantane and subsequent displacement by nitrogen nucleophile, see: Barton, D. H. R.; Hay-Motherwell, R. S.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1983, 445
48. Ni, C.; Fettinger, J. C.; Long, G. J.; Brynda, M.; Power, P. P. Chem. Commun. 2008, 6045
49. Cowley, R. E.; DeYonker, N. J.; Eckert, N. A.; Cundari, T. R.; DeBeer, S.; Bill, E.; Ottenwaelder, X.; Flaschenriem, C.; Holland, P. L. Inorg. Chem. 2010, 49, 6172
50. Cowley, R. E.; Holland, P. L. Inorg. Chem. 2012, 51, 8352
51. Verma, A. K.; Nazif, T. N.; Achim, C.; Lee, S. C. J. Am. Chem. Soc. 2000, 122, 11013
52. Brown, S. D.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2003, 125, 322
53. Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2003, 125, 10782
54. Brown, S. D.; Peters, J. C. J. Am. Chem. Soc. 2004, 126, 4538
55. Brown, S. D.; Peters, J. C. J. Am. Chem. Soc. 2005, 127, 1913
56. Mehn, M. P.; Brown, S. D.; Jenkins, D. M.; Peters, J. C.; Que, L., Jr. Inorg. Chem. 2006, 45, 7417
57. Thomas, C. M.; Mankad, N. P.; Peters, J. C. J. Am. Chem. Soc. 2006, 128, 4956
58. Lu, C. C.; Saouma, C. T.; Day, M. W.; Peters, J. C. J. Am. Chem. Soc. 2007, 129, 4
59. Nieto, I.; Ding, F.; Bontchev, R. P.; Wang, H.; Smith, J. M. J. Am. Chem. Soc. 2008, 130, 2716
60. Bowman, A. C.; Milsmann, C.; Bill, E.; Turner, Z. R.; Lobkovsky, E.; DeBeer, S.; Wieghardt, K.; Chirik, P. J. J. Am. Chem. Soc. 2011, 133, 17353
61. Moret, M.-E.; Peters, J. C. Angew. Chem., Int. Ed. 2011, 50, 2063
62. Mehn, M. P.; Peters, J. C. J. Inorg. Biochem. 2006, 100, 634
63. Holland, P. L. Acc. Chem. Res. 2008, 41, 905
64. Berry, J. F. Comments Inorg. Chem. 2009, 30, 28
65. Saouma, C. T.; Peters, J. C. Coord. Chem. Rev. 2011, 255, 920
66. Cowley, R. E.; Holland, P. L. Inorg. Chim. Acta 2011, 369, 40
67. Cowley, R. E.; Eckert, N. A.; Vaddadi, S.; Figg, T. M.; Cundari, T. R.; Holland, P. L. J. Am. Chem. Soc. 2011, 133, 9796
68. Lucas, R. L.; Powell, D. R.; Borovik, A. S. J. Am. Chem. Soc. 2005, 127, 11596
69. Eckert, N. A.; Vaddadi, S.; Stoian, S.; Lachicotte, R. J.; Cundari, T. R.; Holland, P. L. Angew. Chem., Int. Ed. 2006, 45, 6868
70. 3)-H bond of the co-ligand, see: King, E. R.; Betley, T. A. Inorg. Chem. 2009, 48, 2361
71. Klinker, E. J.; Jackson, T. A.; Jensen, M. P.; Stubna, A.; Juhász, G.; Bominaar, E. L.; Münck, E.; Que, L., Jr. Angew. Chem., Int. Ed. 2006, 45, 7394
72. Jensen, M. P.; Mehn, M. P.; Que, L., Jr. Angew. Chem., Int. Ed. 2003, 42, 4357
73. Avenier, F.; Gouré, E.; Dubourdeaux, P.; Sénèque, O.; Oddou, J.-L.; Pécaut, J.; Chardon-Noblat, S.; Deronzier, A.; Latour, J.-M. Angew. Chem., Int. Ed. 2008, 47, 715
74. 3)-H bond of a pendant adamantyl group in the co-ligand. See: Hatanaka, T.; Miyake, R.; Ishida, Y.; Kawaguchi, H. J. Organomet. Chem. 2011, 696, 4046
75. 3)-H bond (∼76-86 kcal/mol). See: Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007.
76. Breslow, R.; Gellman, S. H. J. Chem. Soc., Chem. Commun. 1982, 1400
77. Svastits, E. W.; Dawson, J. H.; Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1985, 107, 6427
78. Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. New J. Chem. 1989, 13, 651
79. Liu, Y.; Che, C.-M. Chem.-Eur. J. 2010, 16, 10494
80. Liu, Y.; Wei, J.; Che, C.-M. Chem. Commun. 2010, 46, 6926
81. Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036
82. Groves, J. T.; Van Der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290
83. Vincent, J. B.; Huffman, J. C.; Christou, G.; Li, Q.; Nanny, M. A.; Hendrickson, D. N.; Fong, R. H.; Fish, R. H. J. Am. Chem. Soc. 1988, 110, 6898
84. Tung, H.-C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445
85. Leising, R. A.; Kim, J.; Pérez, M. A.; Que, L., Jr. J. Am. Chem. Soc. 1993, 115, 9524
86. Kojima, T.; Leising, R. A.; Yan, S.; Que, L., Jr. J. Am. Chem. Soc. 1993, 115, 11328
87. Kim, J.; Harrison, R. G.; Kim, C.; Que, L., Jr. J. Am. Chem. Soc. 1996, 118, 4373
88. Mukerjee, S.; Stassinopoulos, A.; Caradonna, J. P. J. Am. Chem. Soc. 1997, 119, 8097
89. Kim, C.; Chen, K.; Kim, J.; Que, L., Jr. J. Am. Chem. Soc. 1997, 119, 5964
90. Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. J. Am. Chem. Soc. 1999, 121, 9120
91. Leung, S. K.-Y.; Tsui, W.-M.; Huang, J.-S.; Che, C.-M.; Liang, J.-L.; Zhu, N. J. Am. Chem. Soc. 2005, 127, 16629
92. Fantauzzi, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Casati, N.; Macchi, P.; Cenini, S. Chem. Commun. 2009, 3952
93. Wong, E. L.-M.; Fang, G.-S.; Che, C.-M.; Zhu, N. Chem. Commun. 2005, 4578
94. For preparation of qpy ligand, see: Constable, E. C.; Martínez-Máñez, R.; Cargill Thompson, A. M. W.; Walker, J. V. J. Chem. Soc., Dalton Trans. 1994, 1585
95. Tong, G. S. M.; Wong, E.-L. M.; Che, C.-M. Chem.-Eur. J. 2008, 14, 5495
96. Cohen, G. H.; Hoard, J. L. J. Am. Chem. Soc. 1966, 88, 3228
97. Fleischer, E.; Hawkinson, S. J. Am. Chem. Soc. 1967, 89, 720
98. Gusev, D. G.; Hübener, R.; Burger, P.; Orama, O.; Berke, H. J. Am. Chem. Soc. 1997, 119, 3716
99. Maigut, J.; Meier, R.; Zahl, A.; van Eldik, R. J. Am. Chem. Soc. 2008, 130, 14556
100. Soo, H. S.; Sougrati, M. T.; Grandjean, F.; Long, G. J.; Chang, C. J. Inorg. Chim. Acta 2011, 369, 82
101. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935
102. Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2002, 41, 3465
103. Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 9220
104. Milczek, E.; Boudet, N.; Blakey, S. Angew. Chem., Int. Ed. 2008, 47, 6825
105. Fiori, K. W.; Espino, C. G.; Brodsky, B. H.; Du Bois, J. Tetrahedron 2009, 65, 3042
106. Harvey, M. E.; Musaev, D. G.; Du Bois, J. J. Am. Chem. Soc. 2011, 133, 17207
107. Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233
108. Au, S.-M.; Huang, J.-S.; Che, C.-M.; Yu, W.-Y. J. Org. Chem. 2000, 65, 7858
109. Zhang, J.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2005, 46, 5403
110. Barman, D. N.; Nicholas, K. M. Eur. J. Org. Chem. 2011, 908
111. 2, see: Lubben, M.; Meetsma, A.; Wilkinson, E. C.; Feringa, B.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1995, 34, 1512
112. We have only found one report which describes isolation of TsN=NTs, see: Kalita, B.; Lamar, A. A.; Nicholas, K. M. Chem. Commun. 2008, 4291
113. (Kwart, H.; Khan, A. A. J. Org. Chem. 1968, 33, 1537)
114. was subsequently found to be Bs-Bs: Maioli, A. T.; Anselme, J.-P. Tetrahedron Lett. 1995, 36, 1221
115. 2 loss even at -50 C: Bock, H. Angew. Chem., Int. Ed. Engl. 1965, 4, 457
116. 4- p -MeO) has been well documented (see, for example: Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174) and is conceived to be a stronger N-donating ligand than TsN=NTs. To the best of our knowledge, no examples of mononuclear metal complexes with TsN=NTs have been reported in literature
117. Liu, P.; Liu, Y.; Wong, E. L.-M.; Xiang, S.; Che, C.-M. Chem. Sci. 2011, 2, 2187
118. de Oliveira, F. T.; Chanda, A.; Banerjee, D.; Shan, X.; Mondal, S.; Que, L., Jr.; Bominaar, E. L.; Münck, E.; Collins, T. J. Science 2007, 315, 835
119. Lyakin, O. Y.; Bryliakov, K. P.; Britovsek, G. J. P.; Talsi, E. P. J. Am. Chem. Soc. 2009, 131, 10798
120. Rohde, J.-U.; Torelli, S.; Shan, X.; Lim, M. H.; Klinker, E. J.; Kaizer, J.; Chen, K.; Nam, W.; Que, L., Jr. J. Am. Chem. Soc. 2004, 126, 16750
121. Badiei, Y. M.; Siegler, M. A.; Goldberg, D. P. J. Am. Chem. Soc. 2011, 133, 1274
122. Hong, S.; Lee, Y.-M.; Cho, K.-B.; Sundaravel, K.; Cho, J.; Kirn, M. J.; Shin, W.; Nam, W. J. Am. Chem. Soc. 2011, 133, 11876
123. Berry, J. F.; Bill, E.; Bothe, E.; George, S. D.; Mienert, B.; Neese, F.; Wieghardt, K. Science 2006, 312, 1937
124. Frisch, M. J.; Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2011. A complete list of authors is included in the Supporting Information.
125. Shen, M.; Driver, T. G. Org. Lett. 2008, 10, 3367
126. Bonnamour, J.; Bolm, C. Org. Lett. 2011, 13, 2012
127. For a rare example of copper-catalyzed amination of benzylic 1 C-H bond of toluene with PhI=NTs in neat toluene to give the amination product in almost quantitative yield, see: Fructos, M. R.; Trofimenko, S.; Díaz-Requejo, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2006, 128, 11784
128. Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531
129. Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563
130. Zhou, Z.-W.; Zhao, Y.-C.; Yue, Y.; Wu, J.; Yang, M.; Yu, X.-Q. Arkivoc 2005, 130
131. Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507
132. Liang, J.-L.; Yu, X.-Q.; Che, C.-M. Chem. Commun. 2002, 124
133. Duran, F. J.; Ghini, A. A.; Dauban, P.; Dodd, R. H.; Burton, G. J. Org. Chem. 2005, 70, 8613
134. Collet, F.; Lescot, C.; Liang, C.; Dauban, P. Dalton Trans. 2010, 39, 10401
135. Lescot, C.; Darses, B.; Collet, F.; Retailleau, P.; Dauban, P. J. Org. Chem. 2012, 77, 7232
136. Subbaraj, A.; Rao, O. S.; Lwowski, W. J. Org. Chem. 1989, 54, 3945
137. Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809
138. Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899
139. Wetter, C.; Studer, A. Chem. Commun. 2004, 174
140. Díaz-Requejo, M. M.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2003, 125, 12078
141. Li, Z.; Capretto, D. A.; Rahaman, R.; He, C. Angew. Chem., Int. Ed. 2007, 46, 5184
142. Lebel, H.; Huard, K. Org. Lett. 2007, 9, 639
143. Huard, K.; Lebel, H. Chem.-Eur. J. 2008, 14, 6222
144. Wiese, S.; Badiei, Y. M.; Gephart, R. T.; Mossin, S.; Varonka, M. S.; Melzer, M. M.; Meyer, K.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2010, 49, 8850
145. Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378
146. Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 562
147. Badiei, Y. M.; Dinescu, A.; Dai, X.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961
148. Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343
149. Zdilla, M. J.; Abu-Omar, M. M. J. Am. Chem. Soc. 2006, 128, 16971
150. Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1990, 112, 7826
151. Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7195
152. Nam, W.; Valentine, J. S. J. Am. Chem. Soc. 1993, 115, 1772
153. Wang, S. H. L.; Mandimutsira, B. S.; Todd, R.; Ramdhanie, B.; Fox, J. P.; Goldberg, D. P. J. Am. Chem. Soc. 2004, 126, 18
154. Lennartson, A.; McKenzie, C. J. Angew. Chem., Int. Ed. 2012, 51, 6767
155. Li, C.; Wu, W.; Kumar, D.; Shaik, S. J. Am. Chem. Soc. 2006, 128, 394
156. Iuliis, M. Z.-D.; Morris, R. H. J. Am. Chem. Soc. 2009, 131, 11263
157. Gao, H.; Ke, Z.; DeYonker, N. J.; Wang, J.; Xu, H.; Mao, Z.-W.; Phillips, D. L.; Zhao, C. J. Am. Chem. Soc. 2011, 133, 2904
158. Li, C.; Wu, W.; Cho, K.-B.; Shaik, S. Chem.-Eur. J. 2009, 15, 8492
159. Jaccob, M.; Rajaraman, G. Dalton Trans. 2012, 41, 10430
160. Lyaskovskyy, V.; Olivos Suarez, A. I.; Lu, H.; Jiang, H.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2011, 133, 12264
161. Hayton, T. W.; Boncella, J. M.; Scott, B. L.; Palmer, P. D.; Batista, E. R.; Hay, P. J. Science 2005, 310, 1941
162. Hayton, T. W.; Boncella, J. M.; Scott, B. L.; Batista, E. R.; Hay, P. J. J. Am. Chem. Soc. 2006, 128, 10549