The frustrated Lewis pair pathway to methylene phosphonium systems

Chemical Science

Volumn 5, Issue 2, 2014, Pages 797-803

  Hasegawa, Yasuharu ^a   Kehr, Gerald ^a   Ehrlich, Stephan ^b   Grimme, Stefan ^b   Daniliuc, Constantin G ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROGEN; ETHYLENE-BRIDGED; FRUSTRATED LEWIS PAIRS; IMINIUM SALTS; LOW TEMPERATURES; PC BONDS; X-RAY CRYSTAL STRUCTURE ANALYSIS;

ISOMERS;

ETHYLENE;

EID: 84891408860     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc52327f     Document Type: Article

References (42)

1. (a) Imminium Salts in Organic Chemistry, Part 1 ed. H. Böhme and H. G. Viehe, Wiley, New York, 1976;
2. (b) M. Arend, B. Westermann and N. Risch, Modern Variants of the Mannich Reaction, Angew. Chem., Int. Ed., 1998, 37, 1044;
3. (c) S. K. Bur and S. F. Martin, Tetrahedron, 2001, 57, 3221;
4. (d) S. F. Martin, Acc. Chem. Res., 2002, 35, 895;
5. (e) B. Westermann, Angew. Chem., Int. Ed., 2003, 42, 151.
6. (a) U. Heim, H. Pritzkow, H. Schönberg and H. Grützmacher, J. Chem. Soc., Chem. Commun., 1993, 673;
7. (b) A. Igau, A. Baceiredo, H. Grützmacher, H. Pritzkow and G. Bertrand, J. Am. Chem. Soc., 1989, 111, 6853;
8. (c) J. Kapp, C. Schade, A. M. El-Nahasa and P. v. R. Schleyer, Angew. Chem., Int. Ed. Engl., 1996, 35, 2236;
9. (d) M. Ehrig, H. Horn, C. Kölmel and R. Ahlrichs, J. Am. Chem. Soc., 1991, 113, 3701;
10. (e) H. Grützmacher and H. Pritzkow, Angew. Chem., Int. Ed. Engl., 1992, 31, 99;
11. (f) H. Grützmacher and C. M. Marchand, Coord. Chem. Rev., 1997, 163, 287;
12. (g) R. C. Fischer and P. P. Power, Chem. Rev., 2010, 110, 3877.
13. (a) D. W. Stephan and G. Erker, Angew. Chem., Int. Ed., 2010, 49, 46;
14. (b) Frustrated Lewis Pairs I, Uncovering and Understanding in Topics Current Chemistry, ed G. Erker and D. W. Stephan, Springer, Heidelberg, New York, Dordrecht, London, 2013, vol. 332;
15. (c) Frustrated Lewis Pairs II, Expanding the Scope in Topics Current Chemistry, ed G. Erker and D. W. Stephan, Springer, Heidelberg, New York, Dordrecht, London, 2013, vol. 334.
16. P. Spies, G. Erker, G. Kehr, K. Bergander, R. Fröhlich, S. Grimme and D. W. Stephan, Chem. Commun., 2007, 5072.
17. C.M.Mömming, S. Frömel, G. Kehr, R. Fröhlich, S. Grimme and G. Erker, J. Am. Chem. Soc., 2009, 131, 12280.
18. For related examples see e.g. (a) J.-B. Sortais, T. Voss, G. Kehr, R. Fröhlich and G. Erker, Chem. Commun., 2009, 7417;
19. (b) T. Voss, C. Chen, G. Kehr, E. Nauha, G. Erker and D. W. Stephan, Chem.-Eur. J., 2010, 16, 3005;
20. (c) C. M. Mömming, G. Kehr, R. Fröhlich and G. Erker, Chem. Commun., 2011, 47, 2006.
21. (a) H. Alan, A. H. Cowley, N. C. Norman, M. Pakulski, G. Becker, M. Layh, E. Kirchner and M. Schmidt, Inorg. Synth., 1990, 27, 235;
22. (b) R. Knorr, C. Pires, C. Behringer, T. Menke, J. Freudenreich, E. C. Rossmann and P. Böhrer, J. Am. Chem. Soc., 2006, 128, 14845.
23. (a) D. J. Parks, R. E. von, H. Spence and W. E. Piers, Angew. Chem., Int. Ed. Engl., 1995, 34, 809;
24. (b) W. E. Piers, D. J. Parks and G. P. A. Yap, Organometallics, 1998, 17, 5492.
25. D. G. Yakhvarov, E. Hey-Hawkins, R. M. Kagirov, Y. H. Budnikova, Y. S. Ganushevich and O. G. Sinyashin, Russ. Chem. Bull., 2007, 56, 935.
26. K. Axenov, C. M. Mömming, G. Kehr, R. Fröhlich and G. Erker, Chem.-Eur. J., 2010, 16, 14069.
27. S. Schwendemann, R. Fröhlich, G. Kehr and G. Erker, Chem. Sci., 2011, 2, 1842.
28. (a) V. N. Staroverov, G. E. Scuseria, J. Tao and J. P. Perdew, J. Chem. Phys., 2003, 119, 12129;
29. (b) F. Weigend and R. Ahlrichs, Phys. Chem. Chem. Phys., 2005, 7, 3297;
30. (c) S. Grimme, J. Antony, S. Ehrlich and H. Krieg, J. Chem. Phys., 2010, 132, 154104;
31. (d) S. Grimme, Chem.-Eur. J., 2012, 18, 9955;
32. (e) A. Klamt, Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2011, 1, 699;
33. (a) G. C. Welch, R. R. S. Juan, J. D. Masuda and D. W. Stephan, Science, 2006, 314, 1124;
34. (b) G. C. Welch and D. W. Stephan, J. Am. Chem. Soc., 2007, 129, 1880.
35. See e.g. (a) D. C. R. Hockless, Y. B. Kang, M. A. McDonald, M. Pabel, A. C. Willis and S. B. Wild, Organometallics, 1996, 15, 1301;
36. (b) K. S. Fongers, H. Hogeveen and R. F. Kingma, Tetrahedron Lett., 1983, 24, 643;
37. (c) N. E. Brasch, I. G. Hamilton, E. H. Krenske and S. B. Wild, Organometallics, 2004, 23, 299;
38. (d) O. Ekkert, G. Kehr, R. Fröhlich and G. Erker, Chem. Commun., 2011, 47, 10482.
39. See e.g. (a) E. Otten, R. C. Neu and D. W. Stephan, J. Am. Chem. Soc., 2009, 131, 9918;
40. (b) C. M. Mömming, E. Otten, G. Kehr, R. Fröhlich, S. Grimme, D. W. Stephan and G. Erker, Angew. Chem., Int. Ed., 2009, 48, 6643;
41. (c) M. Sajid, A. Stute, A. J. P. Cardenas, B. J. Culotta, J. A. M. Hepperle, T. H. Warren, B. Schirmer, S. Grimme, A. Studer, C. G. Daniliuc, R. Fröhlich, J. L. Petersen, G. Kehr and G. Erker, J. Am. Chem. Soc., 2012, 134, 10156;
42. (d) M. Sajid, L.-M. Elmer, C. Rosorius, C. G. Daniliuc, S. Grimme, G. Kehr and G. Erker, Angew. Chem., Int. Ed., 2013, 52, 2243.