Iron-catalyzed dehydrocoupling/dehydrogenation of amine-boranes

Journal of the American Chemical Society

Volumn 136, Issue 8, 2014, Pages 3048-3064

  Vance, James R ^a   Schäfer, André ^a   Robertson, Alasdair P M ^a   Lee, Kajin ^a   Turner, Joshua ^a   Whittell, George R ^a   Manners, Ian ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORON COMPOUNDS; CATALYSTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION INTERMEDIATES;

IN-SITU ANALYSIS; IRON CARBONYL COMPLEXES; IRON NANOPARTICLES; MECHANISTIC STUDIES; PHOTO ACTIVATIONS; PHOTO-IRRADIATION; REACTION MIXTURE; TWO-STEP MECHANISMS;

IRON COMPOUNDS;

AMINE; BORANE DERIVATIVE; BORON; CARBONYL IRON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DEHYDROCOUPLING; DEHYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOACTIVATION;

EID: 84896810055     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja410129j     Document Type: Article

References (139)

1. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902-4911
2. Fihri, A.; Bouhrara, M.; Nekoueishahraki, B.; Basset, J.-M.; Polshettiwar, V. Chem. Soc. Rev. 2011, 40, 5181-5203
3. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2000, 34, 18-29
4. Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633
5. Kress, S.; Blechert, S. Chem. Soc. Rev. 2012, 41, 4389-4408
6. Eisch, J. J. Organometallics 2012, 31, 4917-4932
7. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217-254
8. Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624-629
9. Bauer, E. B. Curr. Org. Chem. 2008, 12, 1341-1369
10. Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulous, A. A.; Frost, R. M.; Hird, M. J. Org. Chem. 2006, 71, 1104-1110
11. Hudson, R.; Hamasaka, G.; Osako, T.; Yamada, Y. M. A.; Li, C.-J.; Uozami, Y.; Moores, A. Green. Chem. 2013, 15, 2141-2148
12. Bullock, R. M. Science 2013, 342, 1054-1055
13. Jagadeesh, R. V.; Surkus, A.-E.; Junge, H.; Pohl, M.-M.; Radnik, J.; Rabeah, J.; Huan, H.; Schünemann, V.; Brückner, A.; Beller, M. Science 2013, 342, 1073-1076
14. Friedfield, M. R.; Shevlin, M.; Hoyt, J. M.; Krska, S. W.; Tudge, M. T.; Chirik, P. J. Science 2013, 342, 1076-1080
15. Zuo, W.; Lough, A. J.; Li, Y. F.; Morris, R. H. Science 2013, 342, 1080-1083
16. Clark, T. J.; Lee, K.; Manners, I. Chem.-Eur. J. 2006, 12, 8634-8648
17. Less, R. J.; Melen, R. L.; Wright, D. S. RSC Adv. 2012, 2, 2191-2199
18. Waterman, R. Chem. Soc. Rev. 2013, 42, 5629-5641
19. Leitao, E. M.; Jurca, T.; Manners, I. Nature Chem. 2013, 5, 817-829
20. Hutchins, R. O.; Learn, K.; Nazer, B.; Pytlewski, D.; Pelter, A. Org. Prep. Proced. Int. 1984, 16, 335-372
21. Lane, C. F. Aldrichimica Acta 1973, 6, 51-58
22. Bartoli, G.; Bartolacci, M.; Giuliani, A.; Marcantoni, E.; Massaccesi, M. Eur. J. Org. Chem. 2005, 2867-2879
23. Pasumansky, L.; Goralski, C. T.; Singaram, B. Org. Process. Res. Dev. 2006, 10, 959-970
24. Kanth, J. V. B. Aldrichimica Acta 2002, 35, 57-66
25. Beachley, O. T., Jr.; Washburn, B. Inorg. Chem 1975, 14, 120-123
26. Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev. 2010, 110, 4079-4124
27. Stephens, F. H.; Pons, V.; Baker, R. T. Dalton Trans. 2007, 2613-2626
28. Smythe, N. C.; Gordon, J. C. Eur. J. Inorg. Chem. 2010, 509-521
29. Sutton, A. D.; Burrell, A. K.; Dixon, D. A.; Garner, E. B., III; Gordon, J. C.; Nakagawa, T.; Ott, K. C.; Robinson, P.; Vasiliu, M. Science 2011, 331, 1426-1429
30. Wright, N. R. H.; Berkeley, E. R.; Alden, L. R.; Baker, R. T.; Sneddon, L. G. Chem Commun. 2011, 47, 3177-3179
31. Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 2698-2699
32. Sloan, M. E.; Staubitz, A.; Lee, K.; Manners, I. Eur. J. Org. Chem. 2011, 2011, 672-675
33. Yang, X.; Fox, T.; Berke, H. Chem. Commun. 2011, 47, 2053-2055
34. Yang, X.; Fox, T.; Berke, H. Org. Biomol. Chem. 2012, 10, 852-860
35. Robertson, A. P. M.; Leitao, E. M.; Manners, I. J. Am. Chem. Soc. 2011, 133, 19322-19325
36. Leitao, E. M.; Stubbs, N. E.; Robertson, A. P. M.; Helten, H.; Cox, R. J.; Lloyd-Jones, G. C.; Manners, I. J. Am. Chem. Soc. 2012, 134, 16805-16816
37. Yang, X.; Zhao, L.; Fox, T.; Wang, Z.-X.; Berke, H. Angew. Chem., Int. Ed. 2010, 49, 2058-2062
38. Staubitz, A.; Soto, A. P.; Manners, I. Angew. Chem., Int. Ed. 2008, 47, 6212-6215
39. Dietrich, B. L.; Goldberg, K. I.; Heinekey, D. M.; Autrey, T.; Linehan, J. C. Inorg. Chem. 2008, 47, 8583-8585
40. Staubitz, A.; Sloan, M. E.; Robertson, A. P. M.; Friedrich, A.; Schneider, S.; Gates, P. J.; Schmedt auf der Günne, J.; Manners, I. J. Am. Chem. Soc. 2010, 132, 13332-13345
41. Liu, Z.; Song, L.; Zhao, S.; Huang, J.; Ma, L.; Zhang, J.; Lou, J.; Ajayan, P. M. Nano Lett. 2011, 11, 2032-2037
42. Ewing, W. C.; Marchione, A.; Himmelberger, D. W.; Carroll, P. J.; Sneddon, L. G. J. Am. Chem. Soc. 2011, 133, 17093-17099
43. Liptrot, D. L.; Hill, M. S.; Mahon, M. F.; MacDougall, D. J. Chem.-Eur. J. 2010, 16, 8508-8515
44. Hill, M. S.; Kocick-Koln, G.; Robinson, T. P. Chem. Commun. 2010, 46, 7587-7589
45. Spielmann, J.; Piesik, D. F.-J.; Harder, S. Chem.-Eur. J. 2010, 16, 8307-8318
46. Spielmann, J.; Harder, S. Dalton Trans. 2011, 40, 8314-8319
47. Appelt, C.; Slootweg, J. C.; Lammertsma, K.; Uhl, W. Angew. Chem., Int. Ed. 2013, 52, 4256-4259
48. Hansmann, M. M.; Melen, R. L.; Wright, D. S. Chem. Sci. 2011, 2, 1554-1559
49. Crowley, H. J.; Holt, M. S.; Melen, R. L.; Rawson, J. M.; Wright, D. S. Chem. Commun. 2011, 47, 2682-2684
50. Less, R. J.; Simmonds, H. R.; Dane, S. B. J.; Wright, D. S. Dalton Trans. 2013, 42, 6337-6343
51. Kawano, Y.; Uruichi, M.; Shimoi, M.; Taki, S.; Kawaguchi, T.; Kakizawa, T.; Ogino, H. J. Am. Chem. Soc. 2009, 131, 14946-14957
52. Kakizawa, T.; Kawano, Y.; Naganeyama, K.; Shimoi, M. Chem. Lett. 2011, 40, 171-173
53. Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. Chem. Commun. 2001, 962-963
54. Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2003, 125, 9424-9434
55. Clark, T. J.; Russell, C. A.; Manners, I. J. Am. Chem. Soc. 2006, 128, 9582-9583
56. Sloan, M. E.; Staubitz, A.; Clark, T. J.; Russell, C. A.; Lloyd-Jones, G. C.; Manners, I. J. Am. Chem. Soc. 2010, 132, 3831-3841
57. Dallanegra, R.; Robertson, A. P. M.; Chaplin, A. B.; Manners, I.; Weller, A. S. Chem. Commun. 2011, 47, 3763-3765
58. Denney, M. C.; Pons, V.; Hebden, T. J.; Heinekey, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2006, 128, 12048-12049
59. Keaton, R. J.; Blacquiere, J. M.; Baker, R. T. J. Am. Chem. Soc. 2007, 129, 1844-1845
60. Baker, R. T.; Gordon, J. C.; Hamilton, C. W.; Henson, N. J.; Lin, P.-H.; Maguire, S.; Murugesu, M.; Scott, B. L.; Smythe, N. C. J. Am. Chem. Soc. 2012, 134, 5598-5609
61. Sonnenberg, J. F.; Morris, R. H. ACS Catalysis 2013, 1092-1102
62. Jiang, Y.; Blacque, O.; Fox, T.; Frech, C. M.; Berke, H. Organometallics 2009, 28, 5493-5504
63. Robertson, A. P. M.; Suter, R.; Chabanne, L.; Whittell, G. R.; Manners, I. Inorg. Chem. 2011, 50, 12680-12691
64. Friedrich, A.; Drees, M.; Schneider, S. Chem.-Eur. J. 2009, 15, 10339-10342
65. Vance, J. R.; Robertson, A. P. M.; Lee, K.; Manners, I. Chem.-Eur. J. 2011, 17, 4099-4103
66. Helten, H.; Dutta, B.; Vance, J. R.; Sloan, M. E.; Haddow, M. F.; Sproules, S.; Collison, D.; Whittell, G. R.; Lloyd-Jones, G. C.; Manners, I. Angew. Chem., Int. Ed. 2013, 52, 437-440
67. Luo, Y.; Ohno, K. Organometallics 2007, 26, 3597-3600
68. Pun, D.; Lobkovsky, E.; Chirik, P. J. Chem. Commun. 2007, 3297-3299
69. Vogt, M.; de Bruin, B.; Berke, H.; Trincado, M.; Grützmacher, H. Chem. Sci. 2011, 2, 723-727
70. Garcia-Vivó, D.; Huergo, E.; Ruiz, M. A.; Travieso-Puente, R. Eur. J. Inorg. Chem. 2013, 4998-5008
71. Chapman, A. M.; Haddow, M. F.; Wass, D. F. J. Am. Chem. Soc. 2011, 133, 8826-8829
72. Tang, C. Y.; Thompson, A. L.; Aldridge, S. J. Am. Chem. Soc. 2010, 132, 10578-10591
73. Duman, S.; Ozkar, S. Int. J. Hydrogen Energ. 2013, 38, 10000-10011
74. Zahmakiran, M.; Ozkar, S. Top. Catal. 2013, 56, 1171-1183
75. Kim, S.-K.; Han, W.-S.; Kim, T.-J.; Kim, T.-Y.; Nam, S. W.; Mitoraj, M.; Piekoś, L.; Michalak, A.; Hwang, S.-J.; Kang, S. O. J. Am. Chem. Soc. 2010, 132, 9954-9955
76. Chaplin, A. B.; Weller, A. S. Angew. Chem., Int. Ed. 2010, 49, 581-584
77. Butera, V.; Russo, N.; Sicilia, E. Chem.-Eur. J. 2011, 17, 14586-14592
78. Paul, A.; Musgrave, C. B. Angew. Chem., Int. Ed. 2007, 46, 8153-8156
79. García-Vivó, D.; Huergo, E.; Ruiz, M. A.; Travieso-Puente, R. Eur. J. Inorg. Chem. 2013, 28, 4998-5008
80. Dallanegra, R.; Chaplin, A. B.; Weller, A. S. Angew. Chem., Int. Ed. 2009, 48, 6875-6878
81. Marziale, A. N.; Friedrich, A.; Klopsch, I.; Drees, M.; Celinski, V.; Schmedt auf der Günne, J.; Schneider, S. J. Am. Chem. Soc. 2013, 135, 13342-13355
82. Dinç, M.; Metin, Ö.; Özkar, S. Catal. Today 2012, 183, 10-16
83. Luo, W.; Campbell, P. G.; Zakharov, L. N.; Liu, S.-Y. J. Am. Chem. Soc. 2011, 133, 19326-19329
84. Aranishi, K.; Jiang, H.-L.; Akita, T.; Haruta, m.; Xu, Q. Nano Res. 2011, 4, 1233-1241
85. Qiu, F.; Li, L.; Wang, Y.; An, C.; Xu, C.; Xu, Y.; Wang, Y.; Jiao, L.; Yuan, H. Int. J. Hydrogen Energy 2013, 38, 7291-7297
86. Wang, H.-L.; Yan, J.-M.; Wang, Z.-L.; Jiang, Q. Int. J. Hydrogen Energy 2012, 37, 10229-10235
87. Qiu, F.; Li, L.; Liu, G.; Wang, Y.; Wang, Y.; An, C.; Xu, Y.; Xu, C.; Wang, Y.; Jiao, L.; Yuan, H. Int. J. Hydrogen Energy 2013, 38, 3241-3249
88. Sewell, L. J.; Lloyd-Jones, G. C.; Weller, A. S. J. Am. Chem. Soc. 2012, 134, 3598-3610
89. Stevens, C. J.; Dallanegra, R.; Chaplin, A. B.; Weller, A. S.; MacGregor, S. A.; Ward, B.; McKay, D.; Alcaraz, G.; Sabo-Etienne, S. Chem.-Eur. J. 2011, 17, 3011-3020
90. Chen, Y.; Fulton, J. L.; Linehan, J. C.; Autrey, T. J. Am. Chem. Soc. 2005, 127, 3254-3255
91. Johnson, H. C; Robertson, A. P. M.; Chaplin, A. B.; Sewell, L. J.; Thompson, A. L.; Haddow, M. F.; Manners, I.; Weller, A. S. J. Am. Chem. Soc. 2011, 133, 11076-11078
92. Huertos, M. A.; Weller, A. S. Chem. Sci. 2013, 4, 1881-1888
93. 2) have been characterized in other research. For a recent paper detailing some examples, see: Helten, H.; Robertson, A. P. M.; Staubitz, A.; Vance, J. R.; Haddow, M. F.; Manners, I. Chem.-Eur. J. 2012, 18, 4665-4680
94. tBu: see ref 49. Sonnenberg, J. F.; Morris, R. H. ACS Catalysis 2013, 1092-1102
95. Nöth, H.; Thomas, S. Eur. J. Inorg. Chem. 1999, 1999, 1373-1379
96. Comprehensive Organometallic Chemistry, 2 nd ed.; Shriver, D. F. B.; Michael, I., Ed.; Pergamon Press: New York, 1995; Vol. 7.
97. Caspar, J. V.; Meyer, T. J. J. Am. Chem. Soc. 1980, 102, 7794-7795
98. Meyer, T. J.; Caspar, J. V. Chem. Rev. 1985, 85, 187-218
99. Dixon, A. J.; George, M. W.; Hughes, C.; Poliakoff, M.; Turner, J. J. J. Am. Chem. Soc. 1992, 114, 1719-1729
100. Douglas, T. M.; Chaplin, A. B.; Weller, A. S. J. Am. Chem. Soc. 2008, 130, 14432-14433
101. Douglas, T. M.; Chaplin, A. B.; Weller, A. S.; Yang, X.; Hall, M. B. J. Am. Chem. Soc. 2009, 131, 15440-15456
102. Alcaraz, G.; Vendier, L.; Colt, E.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2010, 49, 918-920
103. Alcaraz, G.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2010, 49, 7170-7179
104. Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023-4078
105. Stephens, F. H.; Baker, R. T.; Matus, M. H.; Grant, D. J.; Dixon, D. A. Angew. Chem. Int. Ed. 2007, 46, 746-749
106. Hai-Shan, D.; Roberts, B. P. Tetrahedron Lett. 1992, 33, 6169-6172
107. Dang, H.-S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1993, 891-898
108. Bitterwolf, T. E. Coord. Chem. Rev. 2000, 206-207, 419-450
109. Widegren, J. A.; Finke, R. G. J. Mol. Cat. A: Chem. 2003, 198, 317-341
110. Widegren, J. A.; Bennett, M. A.; Finke, R. G. J. Am. Chem. Soc. 2003, 125, 10301-10310
111. Crabtree, R. H. Chem. Rev. 2012, 112, 1536-1554
112. Based on recent work by Amiens and co-workers, the Fe nanoparticles are also anticipated to contain significant amounts of boron (which is difficult to detect by EDX analysis). These workers showed that treatment of Fe(II) salts with amine-boranes led to Fe nanoparticles containing 15-25% B based on EXAFS and Mössbauer spectroscopy. Mechanisms of formation involving the reactions with aminoborane intermediates or products at the nanoparticle nucleation stage or with the Fe nanoparticles themselves were proposed. See: Pellelier, F.; Ciuculescu, D.; Mattei, J.-G.; Lecante, P.; Casanove, M.-J.; Schmitz-Antoniak, C.; Amiens, C. Chem.-Eur. J. 2013, 19, 6021-6026
113. Njagi, E. C.; Huang, H.; Stafford, L.; Genuino, H.; Galindo, H. M.; Collins, J. B.; Hoag, G. E.; Suib, S. L. Langmuir 2011, 27, 264-271
114. Alway, D. G.; Barnett, K. W. Inorg. Chem. 1978, 17, 2826-2831
115. Allen, D. M.; Cox, A.; Kemp, T. J.; Sultana, Q. Inorg. Chim. Acta 1977, 21, 191-194
116. Pan, X.; Philbin, C. E.; Castellani, M. P.; Tyler, D. R. Inorg. Chem. 1988, 27, 671-676
117. Zhang, S.; Brown, T. L. Organometallics 1992, 11, 4166-4173
118. Labinger, J. A.; Madhavan, S. J. Organomet. Chem. 1977, 134, 381-389
119. Hamilton, C. W.; Baker, R. T.; Staubitz, A.; Manners, I. Chem. Soc. Rev. 2009, 38, 279-293
120. Babu Kalidindi, S.; Sanyal, U.; Jagirdar, B. R. ChemSusChem 2011, 4, 317-324
121. Yan, J.-M.; Zhang, X.-B.; Han, S.; Shioyama, H.; Xu, Q. Angew. Chem., Int. Ed. 2008, 47, 2287-2289
122. Clark, T. J.; Whittell, G. R.; Manners, I. Inorg. Chem. 2007, 46, 7522-7527
123. Glavee, G. N.; Klabunde, K. J.; Sorensen, C. M.; Hadjipanayis, G. C. Inorg. Chem. 1995, 34, 28-35
124. Alexandridas, P. Chem. Eng. Technol. 2011, 34, 15-28
125. Virkutyte, J.; Varma, R. S. Chem. Sci. 2011, 2, 837-846
126. Margeat, O.; Dumestre, F.; Amiens, C.; Chaudret, B.; Lecante, P.; Respaud, M. Prog. Solid State Chem. 2005, 33, 71-79
127. Boennemann, H.; Brinkmann, R.; Neiteler, P. Appl. Organometal. Chem 1994, 8, 361-378
128. Boennemann, H.; Braun, G.; Brijoux, W.; Brinkmann, R.; Schulze Tilling, A.; Seevogel, K.; Siepen, K. J. Organomet. Chem. 1996, 520, 143-162
129. Bitterwolf, T. E.; Linehan, J. C.; Shade, J. E. Organometallics 2000, 19, 4915-4917
130. Robertson, A. P. M.; Suter, R.; Chabanne, L.; Whittell, G. R.; Manners, I. Inorg. Chem. 2011, 50, 12680-12691
131. Hill, M. S.; Kociok-Köhn, G.; Robinson, T. P. Chem. Commun. 2010, 46, 7587-7589
132. Beweries, T.; Hansen, S.; Kessler, M.; Klahn, M.; Rosenthal, U. Dalton Trans. 2011, 40, 7689-7692
133. Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 9776-9785
134. Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 1334-1335
135. Fulton, J. L.; Linehan, J. C.; Autrey, T.; Balasubramanian, M.; Chen, Y.; Szymczak, N. K. J. Am. Chem. Soc. 2007, 129, 11936-11949
136. Zahmakiran, M.; Özkaîr, S. Inorg. Chem. 2009, 48, 8955-8964
137. Metin, Ö.; Mazumder, V.; Özkaîr, S.; Sun, S. J. Am. Chem. Soc. 2010, 132, 1468-1469
138. Metin, Ö.; Suman, S.; Dinç, M.; Özkaîr, S. J. Phys. Chem. C 2011, 115, 10736-10743
139. Bayram, E.; Linehan, J. C.; Fulton, J. L.; Roberts, J. A. S.; Szymczak, N. K.; Smurthwaite, T. D.; Özkar, S.; Balasubramanian, M.; Finke, R. G. J. Am. Chem. Soc. 2011, 133, 18889-18902