Low-temperature addition of organolithiums to functionalized vinylsilanes under formation of secondary α-lithiated alkylsilanes

Journal of the American Chemical Society

Volumn 131, Issue 47, 2009, Pages 17044-17045

  Unkelbach, Christian ^a   Strohmann, Carsten ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLLITHIUMS; ALKYLSILANES; APOLAR SOLVENTS; CARBOLITHIATION; CHEMICAL EQUATIONS; ENERGETIC BARRIERS; FUNCTIONALIZED; LOW TEMPERATURES; METHYLLITHIUM; ORGANOLITHIUMS; STRUCTURAL MOTIFS; VINYL SILANE;

SILANES;

CHEMICAL REACTIVITY;

ORGANOLITHIUM COMPOUND; SILANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CARBOLITHIATION; ENERGY TRANSFER; LITHIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 72249114027     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9076167     Document Type: Article

References (32)

1. (a) Peterson, D. J. J. Org. Chem. 1968, 33, 780.
2. (b) van Staden, L. F.; Gravestock, D.; Ager, D. J. Chem. Soc. Rev. 2002, 31, 195.
3. (a) Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8738.
4. (b) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
5. (c) Itami, K.; Kamei, T.; Mitsudo, K.; Nokami, T.; Yoshida, J. J. Org. Chem. 2001, 66, 3970.
6. (a) Tamao, K.; Takui, T.; Kumada, M. J. Am. Chem. Soc. 1978, 11, 2268.
7. (b) Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317.
8. (a) Cason, L. F.; Brooks, H. G. J. Org. Chem. 1952, 74, 4582.
9. (b) Ager, D. J. J. Chem. Soc., Perkin Trans. 1 1983, 1131.
10. (c) Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440.
11. (d) van der Leij, M.; Zwanenburg, B. Tetrahedron Lett. 1978, 36, 3383.
12. (a) Stey, T.; Stalke, D. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley, Chichester, 2004; pp 47-120.
13. (b) Strohmann, C.; Gessner, V. H. J. Am. Chem. Soc. 2007, 129, 8952.
14. (c) Gessner, V. H.; Daeschlein, C.; Strohmann, C. Chem. - Eur. J. 2009, 15, 3320.
15. (a) Köhler, F. H.; Hertkorn, N.; Blümel, J. Chem. Ber. 1987, 120, 2081.
16. (b) Strohmann, C.; Gessner, V. H. J. Am. Chem. Soc. 2008, 130, 14412.
17. (a) Luitjes, H.; Schakel, M.; Aarnts, M. P.; Schmitz, R. F.; de Kanter, F. J. J.; Klumpp, G. W. Tetrahedron 1997, 53, 9977.
18. (b) Strohmann, C.; Gessner, V. H. Angew. Chem., Int. Ed. 2007, 119, 4650.
19. Keller, E. Schakal99; University of Freiburg: Freiburg, Germany, 1999.
20. 2 stream), using the X-TEMP 2 device (Kottke, T.; Stalke, D. J. Appl. Crystallogr. 1993, 26, 615. )X-ray crystallography data for 7a and 7f have been deposited with the Cambridge Crystallographic Data Center as supplementary publication Nos.CCDC 746533 (7a) and CCDC 746534 (7f).
21. Ott, H.; Daeschlein, C.; Leusser, D.; Schildbach, D.; Seibel, T.; Stalke, D.; Strohmann, C. J. Am. Chem. Soc. 2008, 130, 11901.
22. Frisch, M. J.; et al. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
23. Schildbach, D.; Arroyo, M.; Lehmen, K.; Martín-Barrios, S.; Sierra, L.; Villafañe, F.; Strohmann, C. Organometallics 2004, 23, 3228.
24. Portmann, S. Molekel; ETH: Zürich, Switzerland, 2001.
25. Additional data sets containing the energies of the respective reactions of 4a and t-BuLi can be found in the Supporting Information.
26. (a) Strohmann, C.; Seibel, T.; Strohfeldt, K. Angew. Chem., Int. Ed. 2003, 42, 4531.
27. (b) Strohmann, C.; Gessner, V. H. Angew. Chem., Int. Ed. 2007, 46, 8281.
28. Experimental procedures and results on competitive carbolithiation of vinylsilanes 4a,b and 6 and MeLi and t-BuLi are described in the Supporting Information.
29. Liu, H.; Deng, K.; Cohen, T.; Jordan, K. D. Org. Lett. 2007, 9, 1911.
30. Norsikian, S.; Marek, I.; Klein, S.; Poisson, J. F; Normant, J. F. Chem. - Eur. J. 1999, 5, 2055.
31. (a) Norsikian, S.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 7523.
32. (b) Hogan, A.-M. L.; Tricotet, T; Meek, A.; Khokar, S. S.; O'Shea, D. F. J. Org. Chem. 2008, 73, 6041.