Tris(5,6,7,8-tetrafluoronaphthalen-2-yl)borane, a partially fluorinated boron lewis acid with fluorination distal to the boron atom

Organometallics

Volumn 33, Issue 5, 2014, Pages 1108-1111

  Mohr, Jens ^a   Durmaz, Mustafa ^a   Irran, Elisabeth ^a   Oestreich, Martin ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON-DEFICIENT; LEWIS ACIDIC; LEWIS ACIDIC CENTERS; LEWIS ACIDITY; MODEL SYSTEM; PARTIALLY FLUORINATED; PHOSPHINE OXIDE; TRIS(PENTAFLUOROPHENYL) BORANE;

CHEMICAL BONDS; FLUORINATION; FLUORINE; HALOGENATION; PHOSPHORUS COMPOUNDS; SILICON;

BORON;

EID: 84896751551     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500128a     Document Type: Article

References (57)

1. Frustrated Lewis Pairs I, Uncovering and Understanding; Erker, G.; Stephan, D. W., Eds.; Topics in Current Chemistry 332; Springer: Heidelberg, Germany, 2013.
2. Frustrated Lewis Pairs II, Expanding the Scope; Erker, G.; Stephan, D. W., Eds.; Topics in Current Chemistry 334; Springer: Heidelberg, Germany, 2013. For a review, see
3. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
4. Massey, A. G.; Park, A. J.; Stone, F. G. A. Proc. Chem. Soc. 1963, 212
5. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245-250
6. Erker, G. Dalton Trans. 2005, 1883-1890
7. Piers, W. E. Adv. Organomet. Chem. 2004, 52, 1-76
8. Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345-354
9. Yang, X.; Stern, C.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 3623-3625
10. Marks, T. J. Acc. Chem. Res. 1992, 25, 65-71
11. Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-10031
12. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1755-1757
13. Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451-12452
14. Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440-9441
15. Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887-4892
16. Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. E. Org. Lett. 2000, 2, 3921-3923
17. Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090-3098
18. Rendler, S.; Oestreich, M. Angew. Chem., Int. Ed. 2008, 47, 5997-6000
19. Hog, D. T.; Oestreich, M. Eur. J. Org. Chem. 2009, 5047-5056
20. Sakata, K.; Fujimoto, H. J. Org. Chem. 2013, 78, 12505-12512
21. Hermeke, J.; Mewald, M.; Oestreich, M. J. Am. Chem. Soc. 2013, 135, 17537-17546
22. Robert, T.; Oestreich, M. Angew. Chem., Int. Ed. 2013, 52, 5216-5218
23. Piers, W. E.; Marwitz, A. J. V.; Mercier, L. G. Inorg. Chem. 2011, 50, 12252-12262
24. 3]
25. 3]
26. 3]
27. 3]
28. 3]
29. 3]
30. Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451-12452
31. Metz, M. V.; Schwartz, D. J.; Stern, C. L.; Nickias, P. N.; Marks, T. J. Organometallics 2000, 19, 3332-3337
32. Mewald, M.; Fröhlich, R.; Oestreich, M. Chem.-Eur. J. 2011, 17, 9406-9414
33. Mewald, M.; Oestreich, M. Chem.-Eur. J. 2012, 18, 14079-14084
34. Liu, Y.; Du, H. J. Am. Chem. Soc. 2013, 135, 6810-6813
35. Morrison, D. J.; Piers, W. E.; Parvez, M. Synlett 2004, 2429-2433
36. Li, L.; Marks, T. J. Organometallics 1998, 17, 3996-4003
37. Borane 5 is mentioned in a patent, but no detailed synthesis is reported: Rodriguez, G.; Rix, F. C.; Ravishankar, P. S.; Kuchta, M. C. Partially Fluorinated Naphthyl-Based Borates. PCT Int. Appl. WO 03/051892 A1, 2003.
38. Coe, P. L.; Pearl, G. M.; Tatlow, J. C. J. Chem. Soc. C 1971, 604-608
39. Yudin, A. K.; Martyn, L.; James, P.; Pandiaraju, S.; Zheng, J.; Lough, A. Org. Lett. 2000, 2, 41-44
40. Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem. 2000, 65, 164-168
41. Iimura, S.; Wu, W. Tetrahedron Lett. 2010, 51, 1353-1355
42. Thompson, A. L. S.; Kabalka, G. W.; Akula, M. R.; Huffmann, J. W. Synthesis 2005, 547-550
43. Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333-3336
44. Parks, D. J.; Spence, R. E. v. H.; Piers, W. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 809-811
45. Metz, M. V.; Schwartz, D. J.; Stern, C. L.; Nickias, P. N.; Marks, T. J. Angew. Chem., Int. Ed. 2000, 39, 1312-1316
46. Chase, P. A.; Piers, W. E.; Patrick, B. O. J. Am. Chem. Soc. 2000, 122, 12911-12912
47. Bergquist, C.; Bridgewater, B. M.; Harlan, C. J.; Norton, J. R.; Friesner, R. A.; Parkin, G. J. Am. Chem. Soc. 2000, 122, 10581-10590
48. Beringhelli, T.; Maggioni, D.; D'Alfonso, G. Organometallics 2001, 20, 4927-4938
49. Gutmann, V. Coord. Chem. Rev. 1976, 18, 225-255
50. Beckett, M. A.; Brassington, D. S.; Light, M. E.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 2001, 1768-1772
51. Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801-808
52. Britovsek, G. J. P.; Ugolotti, J.; White, A. J. P. Organometallics 2005, 24, 1685-1691
53. Herrington, T. J.; Thom, A. J. W.; White, A. J. P.; Ashley, A. E. Dalton Trans. 2012, 41, 9019-9022
54. Welch, G. C.; Cabrera, L.; Chase, P. A.; Hollink, E.; Masuda, J. D.; Wei, P.; Stephan, D. W. Dalton Trans. 2007, 3407-3414
55. Sivaev, I. B.; Bregadze, V. I. Coord. Chem. Rev. DOI: 10.1016/j.ccr.2013.10.017.
56. Horton, A. D.; de With, J. Organometallics 1997, 16, 5424-5436
57. Beringhelli, T.; Donghi, D.; Maggioni, D.; D'Alfonso, G. Coord. Chem. Rev. 2008, 252, 2292-2313