Silylium ion/phosphane lewis pairs

Organometallics

Volumn 32, Issue 22, 2013, Pages 6736-6744

  Reißmann, Matti ^a   Schäfer, André ^a   Jung, Sebastian ^a   Müller, Thomas ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT CONDITIONS; DIHYDROGEN; FRUSTRATED LEWIS PAIRS; MOLECULAR HYDROGEN; PROTON AFFINITY; STERIC FACTOR; STERIC HINDRANCES; TRIARYLSILYLIUM IONS;

CARBON DIOXIDE; CHEMICAL REACTIONS;

IONS;

EID: 84888632816     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om400559x     Document Type: Article

References (79)

1. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
2. Erker, G. C. R. Chim. 2011, 14, 831
3. 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.; Ullrich, M. Inorg. Chem. 2011, 50, 12338
4. Erker, G. Dalton Trans. 2011, 40, 7475
5. Stephan, D. W. Org. Biomol. Chem. 2012, 10, 5740
6. Brown, H. C.; Schlesinger, H. I.; Cardon, S. Z. J. Am. Chem. Soc. 1942, 64, 325
7. Brown, H. C.; Kanner, B. J. Am. Chem. Soc. 1966, 88, 986
8. Wittig, G.; Reppe, H. G.; Eicher, T. Liebigs Ann. Chem. 1961, 643, 47
9. Tochtermann, W. Angew. Chem., Int. Ed. 1966, 5, 351
10. Stephan, D. W. Chem. Commun. 2010, 46, 8526
11. Welch, G. C.; San Juan, R. R.; Masuda, J. D.; Stephan, D. W. Science 2007, 314, 1124
12. Welch, G. C.; Stephan, D. W. J. Am. Chem. Soc. 2007, 129, 1880
13. Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008, 1701
14. Sumerin, V.; Schulz, F.; Atsumi, M.; Wang, C.; Nieger, M.; Leskelä, M.; Repo, T.; Pyykkö, P.; Rieger, B. J. Am. Chem. Soc. 2008, 130, 14117
15. Axenov, G. V.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2009, 131, 3454
16. Jiang, C. F.; Blacque, O.; Berke, H. Chem. Commun. 2009, 5518
17. Geier, S. J.; Chase, P. A.; Stephan, D. W. Chem. Commun. 2010, 46, 4884
18. Li, H.; Wen, M.; Lu, G.; Wang, Z.-X. Dalton Trans. 2012, 41, 9091
19. Segawa, Y.; Stephan, D. W. Chem. Commun. 2012, 48, 11963
20. Chen, D.; Wang, Y.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475
21. Chen, D.; Leich, V.; Pan, F.; Klankermayer, J. Chem. Eur. J. 2012, 18, 5184
22. Ghattas, G.; Chen, D.; Pan, F.; Klankermayer, J. Dalton Trans. 2012, 41, 9026
23. Mömming, C.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643
24. Ashley, A. E.; Thompson, A. L.; O'Hare, D. Angew. Chem., Int. Ed. 2009, 48, 9839
25. Dureen, M. A.; Stephan, D. J. Am. Chem. Soc. 2010, 132, 13559
26. Berkefeld, A.; Piers, W. E.; Parvez, M. J. Am. Chem. Soc. 2010, 132, 1796
27. András, R. T.; Hamza, A.; András, S.; Soós, T.; Pápai, I. Angew. Chem., Int. Ed. 2008, 47, 2435
28. Bakó, I.; Stirling, A.; Bálint, S.; Pápai, I. Dalton Trans. 2012, 30, 9023
29. Hamza, A.; Stirling, A.; Rokob, T. A.; Pápai, I. Int. J. Quantum Chem. 2009, 109, 2416
30. Rokob, T. A.; Bakó, I.; Stirling, A.; Hamza, A.; Pápai, I. J. Am. Chem. Soc. 2013, 135, 4425
31. Grimme, S.; Kruse, H.; Goerigk, L.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 1402
32. Schirmer, B.; Grimme, S. Chem. Commun. 2010, 46, 7942
33. Camaioni, D. M.; Ginovska-Pangovska, B.; Schenter, G. K.; Kathmann, S. M.; Autrey, T. J. Phys. Chem. A 2012, 116, 7228
34. Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 8050-8053
35. Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 7543
36. Iglesias-Sigüenza, J.; Alcarazo, M. Angew. Chem., Int. Ed. 2012, 51, 1523
37. Inés, B.; Palomas, D.; Holle, S.; Steinberg, S.; Nicosia, J. A.; Alcarazo, M. Angew. Chem., Int. Ed. 2012, 51, 12367
38. Palomas, D.; Holle, S.; Inés, B.; Bruns, H.; Goddard, R.; Alcarazo, M. Dalton Trans. 2012, 41, 9073
39. Farrell, J. M.; Hatnean, J. A.; Stephan, D. W. J. Am. Chem. Soc. 2012, 134, 15728
40. Freitag, S.; Henning, J.; Schubert, H.; Wesemann, L. Angew. Chem., Int. Ed. 2013, 52, 5640
41. Hounjet, L. J.; Caputo, C. B.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 4714
42. Chapman, A. M.; Haddow, M. F.; Wass, D. F. J. Am. Chem. Soc. 2011, 133, 18463
43. Appelt, C.; Slootweg, J. C.; Lammertsma, K.; Uhl, W. Angew. Chem., Int. Ed. 2012, 51, 5911
44. Appelt, C.; Slootweg, J. C.; Lammertsma, K.; Uhl, W. Angew. Chem., Int. Ed. 2013, 52, 4350
45. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396
46. Menard, G.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 8397
47. Holtrichter-Rößmann, T.; Rösener, C.; Hellmann, J.; Uhl, W.; Würthwein, E.-U.; Fröhlich, R.; Wibbeling, B. Organometallics 2012, 31, 3272
48. Schäfer, A.; Reißmann, M.; Schäfer, A.; Saak, W.; Haase, D.; Müller, T. Angew. Chem., Int. Ed. 2011, 50, 12636
49. Schäfer, A.; Reißmann, M.; Jung, S.; Schäfer, A.; Saak, W.; Brendler, E.; Müller, T. Organometallics 2013, 10.1021/om400366z
50. Rokob, T. A.; Hamza, A.; Pápai, I. J. Am. Chem. Soc. 2009, 131, 10701
51. Müller, T. Adv. Organomet. Chem. 2005, 53, 155
52. Klare, H. F. T.; Oestreich, M. Dalton Trans. 2010, 9176
53. Schäfer, A.; Saak, W.; Haase, D.; Müller, T. Chem. Eur. J. 2009, 15, 3945
54. For an example where silylation of a phosphane was accomplished, see: Driess, M.; Monsé, C.; Merz, K.; van Wüllen, C. Angew. Chem., Int. Ed. 2000, 39, 3684
55. Bartlett, P. D.; Condon, F. E.; Schneider, A. J. Am. Chem. Soc. 1944, 66, 1531
56. Kim, K.-C.; Reed, C. A.; Elliott, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Science 2002, 297, 825
57. Holschumacher, D.; Bannenberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem., Int. Ed. 2008, 47, 7428
58. Douvris, C.; Ozerov, O. V. Science 2008, 321, 1188
59. Scott, V. J.; Çelenligil-Çetin, R.; Ozerov, O. V. J. Am. Chem. Soc. 2005, 127, 2852
60. Gu, W.; Haneline, M. R.; Douvris, C.; Ozerov, O. V. J. Am. Chem. Soc. 2009, 131, 11203
61. Douvris, C.; Nagaraja, C. M.; Chen, C.-H.; Foxman, B. M.; Ozerov, O. V. J. Am. Chem. Soc. 2010, 132, 4946
62. Panisch, R.; Bolte, M.; Müller, T. J. Am. Chem. Soc. 2006, 128, 9676
63. Lühmann, N.; Panisch, R.; Müller, T. Appl. Organomet. Chem. 2010, 24, 533
64. The Gaussian 09, Rev B.01, version of the program was used.
65. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2007, 120, 215
66. Mantina, M.; Chamberlin, A. C.; Valero, R.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. 2009, 113, 5806
67. For an interesting experimental study, see: Marwitz, A. J. V.; Dutton, J. L.; Mercier, L. G.; Piers, W. E. J. Am. Chem. Soc. 2011, 133, 10026
68. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 245
69. Chien, J. C. W.; Tsai, W.-M.; Rausch, M. D. J. Am. Chem. Soc. 1991, 113, 8570
70. Blount, J. F.; Camp, D.; Hart, R. D.; Healy, P. C.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1994, 47, 1631
71. Allman, T.; Goel, R. G. Can. J. Chem. 1982, 60, 716
72. Oliver, K. W.; Rettig, S. J.; Thompson, R. C.; Trotter, J.; Xia, S. J. Fluorine Chem. 1997, 83, 47
73. Ullrich, M.; Lough, A. J.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 52
74. Issleib, K.; Brack, A. Z. Anorg. Allg. Chem. 1954, 277, 258
75. Sasaki, S.; Sutoh, K.; Murakami, F.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 14830
76. Sasaki, S.; Murakami, M.; Murakami, F.; Chowdhury, R.; Sutoh, K.; Yoshifuji, M. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 1477
77. 3SiH comparable to: Lambert, J. B.; Lin, L. Magn. Reson. Chem. 2001, 39, 714
78. 3SiH comparable to: Gynane, M. J. S.; Lappert, M. F.; Riley, P. I. J. Organomet. Chem. 1980, 202, 5
79. Compare to NIST mass spectra (http://webbook.nist.gov/chemistry): n -decylbenzene (NIST MS No. 228246); decan-2-ylbenzene (27554); decan-3-ylbenzene (61119); decan-4-ylbenzene (61118); decan-5-ylbenzene (27555).