Oxidative addition of σ Bonds to an Al(I) center

Journal of the American Chemical Society

Volumn 136, Issue 25, 2014, Pages 9195-9202

  Chu, Terry ^a   Korobkov, Ilia ^b   Nikonov, Georgii I ^a  

^a BROCK UNIVERSITY   (Canada)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRIDES; PHOSPHORUS COMPOUNDS; SILANES; SPECTROSCOPIC ANALYSIS; X RAY DIFFRACTION;

OXIDATIVE ADDITIONS; PHOSPHIDO; PINACOLATE; REDUCTIVE ELIMINATION; SILYL HYDRIDES; SPECTROSCOPIC METHOD;

ALUMINUM;

ALCOHOL; ALUMINUM DERIVATIVE; AMINE; HYDROGEN; PHOSPHINE; SILANE DERIVATIVE;

ARTICLE; ATOM; CHEMICAL STRUCTURE; COVALENT BOND; HYDROGENATION; NEAR INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84903288656     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5038337     Document Type: Article

References (94)

1. Power, P. P. Nature 2010, 463, 171
2. Power, P. P. Chem. Rec. 2012, 12, 238
3. Power, P. P. Acc. Chem. Res. 2011, 44, 627
4. Harder, S. Chem. Rev. 2010, 110, 3852
5. Piers, W. E.; Marwitz, A. J. V.; Mercier, L. G. Inorg. Chem. 2011, 50, 12252
6. Kubas, G. J. Metal Dihydrogen and σ-Bond Complexes: Structure, Theory, and Reactivity; Kluwer: New York, 2001.
7. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2010.
8. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 4 th ed.; Wiley: New York, 2005.
9. Asay, M.; Jones, C.; Driess, M. Chem. Rev. 2010, 111, 354
10. Spikes, G. H.; Fettinger, J. C.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 12232
11. Li, J.; Schenk, C.; Goedecke, C.; Frenking, G.; Jones, C. J. Am. Chem. Soc. 2011, 133, 18622
12. Zhao, L.; Huang, F.; Lu, G.; Wang, Z.-X.; Schleyer, P. v. R. J. Am. Chem. Soc. 2012, 134, 8856
13. Fan, C.; Mercier, L. G.; Piers, W. E.; Tuononen, H. M.; Parvez, M. J. Am. Chem. Soc. 2010, 132, 9604
14. Zhu, Z.; Wang, X.; Peng, Y.; Lei, H.; Fettinger, J. C.; Rivard, E.; Power, P. P. Angew. Chem., Int. Ed. 2009, 48, 2031
15. Caputo, C. A.; Koivistoinen, J.; Moilanen, J.; Boynton, J. N.; Tuononen, H. M.; Power, P. P. J. Am. Chem. Soc. 2013, 135, 1952
16. Seifert, A.; Scheid, D.; Linti, G.; Zessin, T. Chem.-Eur. J. 2009, 15, 12114
17. Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2007, 316, 439
18. Frey, G. D.; Masuda, J. D.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2010, 49, 9444
19. Peng, Y.; Ellis, B. D.; Wang, X.; Power, P. P. J. Am. Chem. Soc. 2008, 130, 12268
20. Peng, Y.; Guo, J.-D.; Ellis, B. D.; Zhu, Z.; Fettinger, J. C.; Nagase, S.; Power, P. P. J. Am. Chem. Soc. 2009, 131, 16272
21. Wang, Y.; Ma, J. J. Organomet. Chem. 2009, 694, 2567
22. Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535
23. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46
24. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124
25. Rokob, T. A.; Hamza, A.; Stirling, A.; Pápai, I. J. Am. Chem. Soc. 2009, 131, 2029
26. Rokob, T. A.; Hamza, A.; Stirling, A.; Soós, T.; Pápai, I. Angew. Chem., Int. Ed. 2008, 47, 2435
27. Grimme, S.; Kruse, H.; Goerigk, L.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 1402
28. 2 activation by a silylium ion, see: Schäfer, A.; Reißmann, M.; Schäfer, A.; Saak, W.; Haase, D.; Müller, T. Angew. Chem., Int. Ed. 2011, 50, 12636
29. For an earlier example of application in catalysis, see: Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 8050
30. Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090
31. Rendler, S.; Oestreich, M. Angew. Chem., Int. Ed. 2008, 47, 5997
32. Blackwell, J. M.; Morrison, D. J.; Piers, W. E. Tetrahedron 2002, 58, 8247
33. Berkefeld, A.; Piers, W. E.; Parvez, M. J. Am. Chem. Soc. 2010, 132, 10660
34. Gevorgyan, V.; Rubin, M.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2001, 66, 1672
35. Rubin, M.; Schwier, T.; Gevorgyan, V. J. Org. Chem. 2002, 67, 1936
36. Gevorgyan, V.; Liu, J.-X.; Rubin, M.; Benson, S.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 8919
37. Sudo, T.; Asao, N.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2494
38. Protchenko, A. V.; Birjkumar, K. H.; Dange, D.; Schwarz, A. D.; Vidovic, D.; Jones, C.; Kaltsoyannis, N.; Mountford, P.; Aldridge, S. J. Am. Chem. Soc. 2012, 134, 6500
39. Dube, J. W.; Brown, Z. D.; Caputo, C. A.; Power, P. P.; Ragogna, P. J. Chem. Commun. 2014, 50, 1944
40. McCarthy, S. M.; Lin, Y.-C.; Devarajan, D.; Chang, J. W.; Yennawar, H. P.; Rioux, R. M.; Ess, D. H.; Radosevich, A. T. J. Am. Chem. Soc. 2014, 136, 4640
41. Zeng, G.; Maeda, S.; Taketsugu, T.; Sakaki, S. Angew. Chem., Int. Ed. 2014, 53, 4633
42. Kurth, F. A.; Eberlein, R. A.; Schnockel, H.; Downs, A. J.; Pulham, C. R. J. Chem. Soc., Chem. Commun. 1993, 1302
43. Chertihin, G. V.; Andrews, L. J. Phys. Chem. 1993, 97, 10295
44. Pullumbi, P.; Bouteiller, Y.; Manceron, L.; Mijoule, C. Chem. Phys. 1994, 185, 25
45. Himmel, H.-J.; Downs, A. J.; Greene, T. M. J. Am. Chem. Soc. 2000, 122, 9793
46. Wang, X.; Andrews, L. J. Phys. Chem. A 2003, 107, 11371
47. Hill, M. S.; Hitchcock, P. B.; Pongtavornpinyo, R. Inorg. Chem. 2007, 46, 3783
48. Cui, C.; Roesky, H. W.; Schmidt, H.-G.; Noltemeyer, M.; Hao, H.; Cimpoesu, F. Angew. Chem., Int. Ed. 2000, 39, 4274
49. Roesky, H. W.; Kumar, S. S. Chem. Commun. 2005, 4027
50. Nagendran, S.; Roesky, H. W. Organometallics 2008, 27, 457
51. Peng, Y.; Fan, H.; Zhu, H.; Roesky, H. W.; Magull, J.; Hughes, C. E. Angew. Chem., Int. Ed. 2004, 43, 3443
52. Zhu, H.; Chai, J.; Fan, H.; Roesky, H. W.; He, C.; Jancik, V.; Schmidt, H.-G.; Noltemeyer, M.; Merrill, W. A.; Power, P. P. Angew. Chem., Int. Ed. 2005, 44, 5090
53. Zhu, H.; Chai, J.; Jancik, V.; Roesky, H. W.; Merrill, W. A.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 10170
54. Cui, C.; Roesky, H. W.; Hao, H.; Schmidt, H.-G.; Noltemeyer, M. Angew. Chem., Int. Ed. 2000, 39, 1815
55. Xiong, Y.; Yao, S.; Driess, M. Chem.-Eur. J. 2012, 18, 3316
56. Yang, Z.; Ma, X.; Oswald, R. B.; Roesky, H. W.; Zhu, H.; Schulzke, C.; Starke, K.; Baldus, M.; Schmidt, H.-G.; Noltemeyer, M. Angew. Chem., Int. Ed. 2005, 44, 7072
57. Dettenrieder, N.; Dietrich, H. M.; Schädle, C.; Maichle- Mössmer, C.; Törnroos, K. W.; Anwander, R. Angew. Chem., Int. Ed. 2012, 51, 4461
58. Dohmeier, C.; Robl, C.; Tacke, M.; Schnöckel, H. Angew. Chem., Int. Ed. 1991, 30, 564
59. Schram, E. P.; Sudha, N. Inorg. Chim. Acta 1991, 183, 213
60. Purath, A.; Dohmeier, C.; Ecker, A.; Schnöckel, H.; Amelunxen, K.; Passler, T.; Wiberg, N. Organometallics 1998, 17, 1894
61. Schnitter, C.; Roesky, H. W.; Röpken, C.; Herbst-Irmer, R.; Schmidt, H.-G.; Noltemeyer, M. Angew. Chem., Int. Ed. 1998, 37, 1952
62. Purath, A.; Schnöckel, H. J. Organomet. Chem. 1999, 579, 373
63. Schiefer, M.; Reddy, N. D.; Roesky, H. W.; Vidovic, D. Organometallics 2003, 22, 3637
64. Fischer, R. A.; Weiß, J. Angew. Chem., Int. Ed. 1999, 38, 2830
65. J Gorden, J. D.; Voigt, A.; Macdonald, C. L. B.; Silverman, J. S.; Cowley, A. H. J. Am. Chem. Soc. 2000, 122, 950
66. Romero, P. E.; Piers, W. E.; Decker, S. A.; Chau, D.; Woo, T. K.; Parvez, M. Organometallics 2003, 22, 1266
67. Beachley, O. T.; Simmons, R. G. Inorg. Chem. 1980, 19, 3042
68. Beachley, O. T.; Rusinko, R. N. Inorg. Chem. 1981, 20, 1367
69. Hallock, R. B.; Beachley, O. T.; Li, Y. J.; Sanders, W. M.; Churchill, M. R.; Hunter, W. E.; Atwood, J. L. Inorg. Chem. 1983, 22, 3683
70. Ganesamoorthy, C.; Loerke, S.; Gemel, C.; Jerabek, P.; Winter, M.; Frenking, G.; Fischer, R. A. Chem. Commun. 2013, 49, 2858
71. Uhl, W.; Jana, B. Chem.-Eur. J. 2008, 14, 3067
72. Uhl, W.; Jana, B. J. Organomet. Chem. 2009, 694, 1101
73. Zhu, H.; Yang, Z.; Magull, J.; Roesky, H. W.; Schmidt, H.-G.; Noltemeyer, M. Organometallics 2005, 24, 6420
74. Atwood, D. A.; Contreras, L.; Cowley, A. H.; Jones, R. A.; Mardones, M. A. Organometallics 1993, 12, 17
75. Janik, J. F.; Wells, R. L.; White, P. S. Inorg. Chem. 1998, 37, 3561
76. Andrews, P. C.; Raston, C. L.; Roberts, B. A. Chem. Commun. 2000, 1961
77. Vogel, U.; Timoshkin, A. Y.; Scheer, M. Angew. Chem., Int. Ed. 2001, 40, 4409
78. Vogel, U.; Timoshkin, A. Y.; Schwan, K.-C.; Bodensteiner, M.; Scheer, M. J. Organomet. Chem. 2006, 691, 4556
79. Bodensteiner, M.; Vogel, U.; Timoshkin, A. Y.; Scheer, M. Angew. Chem., Int. Ed. 2009, 48, 4629
80. For further examples of four-coordinate aluminum phosphides with the average Al-P bond of 2.406 Å, see: Melton, C. E.; Dube, J. W.; Ragogna, P. J.; Fettinger, J. C.; Power, P. P. Organometallics 2014, 33, 329
81. Janik, J. F.; Wells, R. L.; White, P. S. Organometallics 1998, 17, 2361
82. von Hänisch, C.; Rolli, B. Z. Anorg. Allg. Chem. 2004, 630, 1987
83. Seyden-Penne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis; Wiley-VCH: New York, 1997.
84. Healy, M. D.; Mason, M. R.; Gravelle, P. W.; Bott, S. G.; Barron, A. R. J. Chem. Soc., Dalton Trans. 1993, 441
85. Campbell, J. P.; Gladfelter, W. L. Inorg. Chem. 1997, 36, 4094
86. Shekar, S.; Taylor, M. M.; Twamley, B.; Wehmschulte, R. J. Dalton Trans. 2009, 9322
87. Nöth, H.; Schlegel, A.; Knizek, J.; Krossing, I.; Ponikwar, W.; Seifert, T. Chem.-Eur. J. 1998, 4, 2191
88. Shreve, A. P.; Mulhaupt, R.; Fultz, W.; Calabrese, J.; Robbins, W.; Ittel, S. D. Organometallics 1988, 7, 409
89. Clegg, W.; Lamb, E.; Liddle, S. T.; Snaith, R.; Wheatley, A. E. H. J. Organomet. Chem. 1999, 573, 305
90. Benn, R.; Janssen, E.; Lehmkuhl, H.; Rufińska, A.; Angermund, K.; Betz, P.; Goddard, R.; Krüger, C. J. Organomet. Chem. 1991, 411, 37
91. Healy, M. D.; Barron, A. R. Angew. Chem., Int. Ed. 1992, 31, 921
92. APEX Software Suite, v.2010; Bruker AXS: Madison, WI, 2005.
93. Blessing, R. Acta Crystallogr. 1995, A51, 33
94. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112