Frustrated lewis pair reactions with bis-acetylenic substrates: Exploring the narrow gap separating very different competing reaction pathways

Organometallics

Volumn 30, Issue 19, 2011, Pages 5222-5232

  Liedtke, René ^a   Fröhlich, Roland ^a   Kehr, Gerald ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLBORANE; ALKYNYLS; AMBIENT CONDITIONS; HETEROCYCLES; IN-SITU; LEWIS ACID; NARROW GAP; PRODUCT MIXTURE; REACTION PATHWAYS; TRIFLUOROMETHYL; TRIPLE BONDS; TRIS(PENTAFLUOROPHENYL) BORANE; TWO-STEP REACTIONS; X-RAY CRYSTAL STRUCTURE ANALYSIS;

CRYSTAL STRUCTURE; MIXTURES; PHOSPHORUS COMPOUNDS; PHOTOLYSIS; SEMICONDUCTING INDIUM GALLIUM ARSENIDE;

CYCLIZATION;

EID: 80053508911     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200615n     Document Type: Article

References (75)

1. Stute, A.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Commun. 2011, 47, 4288-4290
2. Voss, T.; Sortais, J.-B.; Fröhlich, R.; Kehr, G.; Erker, G. Organometallics 2011, 30, 584-594
3. Zhao, X.; Stephan, D. W. Chem. Commun. 2011, 47, 1833-1835
4. Mömming, C.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Commun. 2011, 47, 2006-2007
5. Birkmann, B.; Voss, T.; Geier, S. J.; Ullrich, M.; Kehr, G.; Erker, G.; Stephan, D. W. Organometallics 2010, 29, 5310-5319
6. Grimme, S.; Kruse, H.; Goerigk, L.; Erker, G. Angew. Chem. 2010, 122, 1444-1447
7. Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6594-6607
8. Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6422-6432
9. Ménard, G.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 1796-1797
10. Appelt, C.; Westenberg, H.; Bertini, F.; Ehlers, A. W.; Slootweg, J. C.; Lammertsma, K.; Uhl, W. Angew. Chem. 2011, 123, 1-5
11. Angew. Chem., Int. Ed. 2011, 50, 1-5.
12. Jiang, C.; Blacque, O.; Fox, T.; Berke, H. Dalton Trans. 2011, 40, 1091-1097
13. Schulz, F.; Sumerin, V.; Leskela, M.; Repo, T.; Rieger, B. Dalton Trans. 2010, 39, 1920-1922
14. Theuergarten, E.; Schlüns, D.; Grunenberg, J.; Daniliuc, G. C.; Jones, P. G.; Tamm, M. Chem. Commun. 2010, 46, 8561-8563
15. Holschumacher, D.; Bannenberg, T.; Ibrom, K.; Daniliuc, G. C.; Jones, P. G.; Tamm, M. Dalton Trans. 2010, 39, 10590-10592
16. Chen, D.; Wang, Y.; Klankermayer, J. Angew. Chem. 2010, 122, 9665-9668
17. Angew. Chem., Int. Ed. 2010, 9665-9668.
18. Erõs, G.; Mehdi, H.; Pápai, I.; Rokob, T. A.; Király, P.; Tárkányi, G.; Soós, T. Angew. Chem. 2010, 122, 6709-6713
19. Angew. Chem., Int. Ed. 2010, 49, 6559-6563.
20. Holschumacher, D.; Taouss, C.; Bannenberg, T.; Hrib, G. C.; Daniliuc, C. G.; Jones, P. G.; Tamm, M. Dalton Trans. 2009, 35, 6927-6929
21. Rokob, T. A.; Hamza, A.; Stirling, A.; Pápai, I. J. Am. Chem. Soc. 2009, 131, 2029-2036
22. Rokob, T. A.; Hamza, A.; Pápai, I. J. Am. Chem. Soc. 2009, 131, 10701-10710
23. Sumerin, V.; Schulz, F.; Nieger, M.; Leskelä, M.; Repo, T.; Rieger, B. Angew. Chem. 2008, 120, 6090-6092
24. Angew. Chem., Int. Ed. 2008, 47, 6001-6003.
25. Stephan, D. W.; Erker, G. Angew. Chem. 2010, 122, 50-81
26. Angew. Chem., Int. Ed. 2010, 49, 46-76.
27. Welch, G. C.; San Juan, R. R.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124-1126
28. Welch, G. C.; Stephan, D. W. J. Am. Chem. Soc. 2007, 129, 1880-1881
29. Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem. 2008, 120, 7654-7657
30. Angew. Chem., Int. Ed. 2008, 47, 7543-7546.
31. Wang, H.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2008, 5966-5968
32. Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem. Commun. 2007, 5072-5074
33. Axenov, K.; Mömming, C. M.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Eur. J. 2010, 16, 14069-14073
34. Moebs-Sanchez, S.; Bouhadir, G.; Saffon, N.; Maron, L.; Bourissou, D. Chem. Commun. 2008, 3435-3437
35. Mömming, C. M.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem. 2009, 121, 6770-6773
36. Angew. Chem., Int. Ed. 2009, 48, 6643-6646.
37. Peuser, I.; Neu, R. C.; Zhao, X.; Ulrich, M.; Schirmer, B.; Tannert, J. A.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G.; Stephan, D. W. Chem. Eur. J. 2011, 17, 9640-9650
38. Otten, E.; Neu, R. C.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 9918-9919
39. Neu, R. C.; Otten, E.; Lough, A.; Stephan, D. W. Chem. Sci. 2011, 2, 170-176
40. McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem. 2007, 119, 5056-5059
41. Angew. Chem., Int. Ed. 2007, 46, 4968-4971.
42. Voss, T.; Chen, C.; Kehr, G.; Nauha, E.; Erker, G.; Stephan, D. W. Chem. Eur. J. 2010, 16, 3005-3008
43. Mömming, C. M.; Frömel, S.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G. J. Am. Chem. Soc. 2009, 131, 12280-12289
44. Mömming, C. M.; Kehr, G.; Wibbeling, B.; Fröhlich, R.; Schirmer, B.; Grimme, S.; Erker, G. Angew. Chem. 2010, 122, 2464-2467
45. Angew. Chem., Int. Ed. 2010, 49, 2414-2417.
46. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396-8397
47. Wrackmeyer, B. Heteroat. Chem. 2006, 17, 188-208
48. Wrackmeyer, B. Coord. Chem. Rev. 1995, 145, 125-156
49. Wrackmeyer, B.; Kenner-Hofmann, B. H.; Milius, W.; Thoma, P.; Tok, O. L.; Herberhold, M. Eur. J. Inorg. Chem. 2006, 101-108
50. Wrackmeyer, B.; Kehr, G.; Sebald, A.; Kümmerlen, J. Chem. Ber. 1992, 125, 1597-1603
51. Wrackmeyer, B.; Kundler, S.; Milius, W.; Boese, R. Chem. Ber. 1994, 127, 333-342
52. Wrackmeyer, B.; Kehr, G.; Boese, R. Angew. Chem. 1991, 103, 1374-1376
53. Angew. Chem., Int. Ed. 1991, 30, 1370-1372.
54. Wrackmeyer, B.; Horchler, K.; Boese, R. Angew. Chem. 1989, 101, 1563-1565
55. Angew. Chem., Int. Ed. 1989, 28, 1500-1502.
56. Chen, C.; Eweiner, F.; Wibbeling, B.; Fröhlich, R.; Senda, S.; Ohki, Y.; Tatsumi, K.; Grimme, S.; Kehr, G.; Erker, G. Chem. Asian J. 2010, 5, 2199-2208
57. Chen, C.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett. 2011, 13, 62-65
58. Jiang, C.; Blacque, O.; Berke, H. Organometallics 2010, 29, 125-133
59. Binnewirtz, R.-J.; Klingenberger, H.; Welte, R.; Paetzold, P. Chem. Ber. 1983, 116, 1271-1284
60. Chen, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2010, 132, 13594-13595
61. Fan, C.; Piers, W. E.; Parvez, M.; McDonald, R. Organometallics 2010, 29, 5132-5139
62. Chen, C.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2010, 46, 3580-3582
63. Tregre, G. J.; Mathias, L. J. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 587-591
64. Labeaume, P.; Wager, K.; Falcone, D.; Li, J.; Torchilin, V.; Castro, C.; Holewa, C.; Kallmerten, A. E.; Jones, G. B. Bioorg. Med. Chem. 2009, 17, 6292-6300
65. Anders, U.; Krause, J.; Wang, D.; Nuyken, O.; Buchmeiser, M. Des. Monomers Polym. 2004, 7, 151-163
66. 3: Wall, L. A.; Donadio, R. E.; Pummer, W. J. J. Am. Chem. Soc. 1960, 82, 4846-4848
67. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 18, 734-736
68. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245-250
69. Massey, A. G.; Park, A. J. Organometallic Syntheses; King, R. B., Eisch, J. J., Eds.; Elsevier: New York,; Vol. 3, pp 461-462.
70. COLLECT; Nonius BV, Delft, The Netherlands, 1998.
71. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326
72. Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr. 2003, A59, 228-234
73. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473
74. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
75. XP; BrukerAXS, Madison, WI, 2000.