One-pot synthesis of [(C6F5)2BH 2]- from C6F5MgBr/BH 3·SMe2 and its in situ transformation to Piers borane

Organometallics

Volumn 30, Issue 10, 2011, Pages 2838-2843

  Schnurr, Anna ^a   Samigullin, Kamil ^a   Breunig, Jens M ^a   Bolte, Michael ^a   Lerner, Hans Wolfram ^a   Wagner, Matthias ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

IN-SITU; ONE-POT REACTION; ONE-POT SYNTHESIS; STARTING MATERIALS;

SYNTHESIS (CHEMICAL);

PIERS;

EID: 79956098298     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200186w     Document Type: Article

References (39)

1. For selected reviews, see: Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345-354
2. Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527-538
3. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434
4. Chivers, T. J. Fluorine Chem. 2002, 115, 1-8
5. Piers, W. E. Adv. Organomet. Chem. 2005, 52, 1-76
6. Focante, F.; Mercandelli, P.; Sironi, A.; Resconi, L. Coord. Chem. Rev. 2006, 250, 170-188
7. Wade, C. R.; Broomsgrove, A. E. J.; Aldridge, S.; Gabbaï, F. P. Chem. Rev. 2010, 110, 3958-3984
8. For reviews on FLPs, see: Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535-1539
9. Stephan, D. W. Dalton Trans. 2009, 3129-3136
10. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
11. Massey, A. G.; Park, A. J.; Stone, F. G. A. Proc. Chem. Soc. 1963, 212
12. Sundararaman, A.; Jäkle, F. J. Organomet. Chem. 2003, 681, 134-142
13. Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451-12452
14. Piers, W. E.; Irvine, G. J.; Williams, V. C. Eur. J. Inorg. Chem. 2000, 2131-2142
15. Qin, Y.; Cheng, G.; Sundararaman, A.; Jäkle, F. J. Am. Chem. Soc. 2002, 124, 12672-12673
16. Roesler, R.; Har, B. J. N.; Piers, W. E. Organometallics 2002, 21, 4300-4302
17. Parks, D. J.; Spence, R. E. v. H.; Piers, W. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 809-811
18. Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem. Commun. 2007, 5072-5074
19. Parks, D. J.; Piers, W. E.; Yap, G. P. A. Organometallics 1998, 17, 5492-5503
20. Jäkle, F. Chem. Rev. 2010, 110, 3985-4022
21. Chambers, R. D.; Chivers, T. J. Chem. Soc. 1965, 3933-3939
22. 2 (which can, moreover, be recycled) gives the target compound in higher purity and better yield. (11)
23. Fuller, A.-M.; Hughes, D. L.; Lancaster, S. J.; White, C. M. Organometallics 2010, 29, 2194-2197
24. Hoshi, M.; Shirakawa, K.; Okimoto, M. Tetrahedron Lett. 2007, 48, 8475-8478
25. Tamborski, C.; Soloski, E. J.; Ward, J. P. J. Org. Chem. 1966, 31, 4230-4232
26. 5/hydride redistribution similar to that exploited in our synthesis: Jiang, C.; Blacque, O.; Berke, H. Organometallics 2009, 28, 5233-5239
27. Biscoe, M. R.; Breslow, R. J. Am. Chem. Soc. 2003, 125, 12718-12719
28. Lorbach, A.; Nadj, A.; Tüllmann, S.; Dornhaus, F.; Schödel, F.; Sänger, I.; Margraf, G.; Bats, J. W.; Bolte, M.; Holthausen, M. C.; Wagner, M.; Lerner, H.-W. Inorg. Chem. 2009, 48, 1005-1017
29. 5MgBr was necessary, because the compound gradually decomposes at elevated temperatures. (17)
30. 2O.
31. Edelstein, N. Inorg. Chem. 1981, 20, 297-299
32. Shannon, R. D. Acta Crystallogr. 1976, A32, 751-767
33. Scheibitz, M.; Bats, J. W.; Bolte, M.; Lerner, H.-W.; Wagner, M. Organometallics 2004, 23, 940-942
34. Scheibitz, M.; Li, H.; Schnorr, J.; Sánchez Perucha, A.; Bolte, M.; Lerner, H.-W.; Jäkle, F.; Wagner, M. J. Am. Chem. Soc. 2009, 131, 16319-16329
35. Eckensberger, U. D.; Weber, M.; Wildt, J.; Bolte, M.; Lerner, H.-W.; Wagner, M. Organometallics 2010, 29, 5301-5309
36. Blessing, R. H. Acta Crystallogr. 1995, A51, 33-38
37. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13
38. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473
39. Sheldrick, G. M. SHELXL-97. A Program for the Refinement of Crystal Structures; Universität Göttingen, Göttingen, Germany, 1997.