Synthesis, structure, and reactivity of a dihydrido borenium cation

Angewandte Chemie - International Edition

Volumn 50, Issue 36, 2011, Pages 8400-8403

  Inés, Blanca ^a   Patil, Mahendra ^a   Carreras, Javier ^a   Goddard, Richard ^a   Thiel, Walter ^a   Alcarazo, Manuel ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

borenium cation; boron; carbodiphosphorane; ligand design; reactive intermediates

Indexed keywords

ANCILLARY LIGANDS; BORENIUM CATION; CARBODIPHOSPHORANE; LIGAND DESIGN; REACTIVE INTERMEDIATE;

BORON; BORON COMPOUNDS; LIGANDS;

POSITIVE IONS;

EID: 80052096528     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103197     Document Type: Article

References (59)

1. P. Kölle, H. Nöth, Chem. Rev. 1985, 85, 399-418
2. for a more recent review on boronium, borenium, and borinium cations, see:, W. E. Piers, S. C. Bourke, K. D. Conroy, Angew. Chem. 2005, 117, 5142-5163
3. Angew. Chem. Int. Ed. 2005, 44, 5016-5036.
4. A. Del Grosso, P. J. Singleton, C. A. Muryn, M. J. Ingleson, Angew. Chem. 2011, 123, 2150-2154
5. Angew. Chem. Int. Ed. 2011, 50, 2102-2106
6. A. Prokofjevs, J. W. Kampf, E. Vedejs, Angew. Chem. 2011, 123, 2146-2149
7. Angew. Chem. Int. Ed. 2011, 50, 2098-2101.
8. N. Kuhn, A. Kuhn, J. Lewandowski, M. Speis, Chem. Ber. 1991, 124, 2197-2201
9. A. H. Cowley, Z. Lu, J. N. Jones, J. A. Moore, J. Organomet. Chem. 2004, 689, 2562-2564
10. I. Ghesner, W. E. Piers, M. Parvez, R. McDonald, Chem. Commun. 2005, 2480-2482
11. C. Bonnier, W. E. Piers, M. Parvez, T. S. Sorensen, Chem. Commun. 2008, 4593-4595
12. C. Bonnier, W. E. Piers, M. Parvez, Organometallics 2011, 30, 1067-1072.
13. C. W. Chiu, F. P. Gabbaï, Angew. Chem. 2007, 119, 1753-1755
14. Angew. Chem. Int. Ed. 2007, 46, 1723-1725
15. C. W. Chiu, F. P. Gabbaï, Organometallics 2008, 27, 1657-1659
16. T. Matsumoto, F. P. Gabbaï, Organometallics 2009, 28, 4252-4253
17. for borenium cations without any π-donor subtituent attached to the boron atom, see Ref. [2b] and, D. McArthur, C. P. Butts, D. M. Lindsay, Chem. Commun. 2011, 47, 6650-6652.
18. T. S. De Vries, E. Vedejs, Organometallics 2007, 26, 3079-3081
19. T. S. De Vries, A. Prokofjevs, J. N. Harvey, E. Vedejs, J. Am. Chem. Soc. 2009, 131, 14679-14687.
20. R. Tonner, G. Frenking, Chem. Eur. J. 2008, 14, 3260-3272
21. R. Tonner, G. Frenking, Chem. Eur. J. 2008, 14, 3273-3289
22. R. Tonner, G. Frenking, Angew. Chem. 2007, 119, 8850-8853
23. Angew. Chem. Int. Ed. 2007, 46, 8695-8698
24. R. Tonner, F. Öxler, B. Neumüller, W. Petz, G. Frenking, Angew. Chem. 2006, 118, 8206-8211
25. Angew. Chem. Int. Ed. 2006, 45, 8038-8042
26. O. Kaufhold, F. E. Hahn, Angew. Chem. 2008, 120, 4122-4126
27. Angew. Chem. Int. Ed. 2008, 47, 4057-4061
28. W. C. Kaska, D. K. Mitchell, R. F. Reichelderfer, J. Organomet. Chem. 1973, 47, 391-402
29. F. E. Hahn, D. Le Van, M. C. Moyes, T. von Ferhen, R. Fröhlich, E. U. Würthwein, Angew. Chem. 2001, 113, 3241-3244
30. Angew. Chem. Int. Ed. 2001, 40, 3144-3148.
31. C. A. Dyker, V. Lavallo, B. Donnadieu, G. Bertrand, Angew. Chem. 2008, 120, 3250-3253
32. Angew. Chem. Int. Ed. 2008, 47, 3206-3209
33. M. Alcarazo, C. W. Lehmann, A. Anoop, W. Thiel, A. Fürstner, Nat. Chem. 2009, 1, 295-301
34. C. A. Dyker, G. Bertrand, Nat. Chem. 2009, 1, 265-266
35. A. Fürstner, M. Alcarazo, R. Goddard, C. W. Lehmann, Angew. Chem. 2008, 120, 3254-3258
36. Angew. Chem. Int. Ed. 2008, 47, 3210-3214
37. M. Melaimi, P. Parameswaran, B. Donnadieu, G. Frenking, G. Bertrand, Angew. Chem. 2009, 121, 4886-4889
38. Angew. Chem. Int. Ed. 2009, 48, 4792-4795
39. J. Vicente, A. R. Singhal, P. G. Jones, Organometallics 2002, 21, 5887-5900
40. M. Alcarazo, C. Gomez, S. Holle, R. Goddard, Angew. Chem. 2010, 122, 5924-5927
41. Angew. Chem. Int. Ed. 2010, 49, 5788-5791
42. H. Bruns, M. Patil, J. Carreras, A. Vázquez, W. Thiel, R. Goddard, M. Alcarazo, Angew. Chem. 2010, 122, 3762-3766
43. Angew. Chem. Int. Ed. 2010, 49, 3680-3683
44. M. Alcarazo, Dalton Trans. 2011, 40, 1839-1845.
45. J. Sundermeyer, K. Weber, K. Peters, H. G. Schnering, Organometallics 1994, 13, 2560-2562.
46. For a former synthesis of 2, see:, W. Petz, F. Öxler, B. Neumüller, R. Tonner, G. Frenking, Eur. J. Inorg. Chem. 2009, 4507-4517.
47. X. Zheng, B. Wang, G. Herberich, Organometallics 2002, 21, 1949-1954, and Ref. [4c].
48. R. Boese, P. Paetzold, A. Tapper, R. Ziembinsky, Chem. Ber. 1989, 122, 1057-1060
49. B. Glaser, E. Hanecker, H. Nöth, H. Wagner, Chem. Ber. 1987, 120, 659-667.
50. D. A. Hoic, J. R. Wolf, W. M. Davis, G. C. Fu, Organometallics 1996, 15, 1315-1318
51. X. Zheng, G. E. Herberich, Organometallics 2000, 19, 3751-3753.
52. S. A. Cummings, M. Iimura, C. J. Harlan, R. J. Kwaan, I. V. Trieu, J. R. Norton, B. M. Bridgewater, F. Jäkle, A. Sundararaman, M. Tilset, Organometallics 2006, 25, 1565-1568.
53. A. Solovyev, Q. Chu, S. J. Geib, L. Fensterbank, M. Malacria, E. Lacôte, D. P. Curran, J. Am. Chem. Soc. 2010, 132, 15072-15080
54. J. Monot, A. Solovyev, H. Bonin-Dubarle, E. Derat, D. P. Curran, M. Robert, L. Fensterbank, M. Malacria, E. Lacôte, Angew. Chem. 2010, 122, 9352-9355
55. Angew. Chem. Int. Ed. 2010, 49, 9166-9169
56. Q. Chu, M. M. Brahmi, A. Solovyev, S. H. Ueng, D. P. Curran, M. Malacria, L. Fensterbank, E. Lacôte, Chem. Eur. J. 2009, 15, 12937-12940.
57. For a recent Review on the synthesis and coordination chemistry of N-heterocyclic carbenes, see:, F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166-3216
58. Angew. Chem. Int. Ed. 2008, 47, 3122-3172.
59. Compound 7 can be also understood as the protonation product of diboranes; see:, Y. Wang, B. Quillian, P. Wie, C. S. Wannere, Y. Xie, R. B. King, H. F. Schaefer III, P. von R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2007, 129, 12412-12413.