Carbon-to-carbon anion relay chemistry: Facile generation of substituted allyllithium species

European Journal of Organic Chemistry

Volumn , Issue 27, 2011, Pages 5255-5260

  Zheng, Pinguan ^a   Cai, Zhengxin ^a   Garimallaprabhakaran, Aswinkumar ^a   Rooshenas, Parham ^b   Schreiner, Peter R ^b   Harmata, Michael ^a  

^a UNIVERSITY OF MISSOURI   (United States)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Carbanions; Density functional calculations; Lithium; Metalation; Silicon

Indexed keywords

EID: 80052479872     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100783     Document Type: Article

References (38)

1. W. H. Moser, Tetrahedron 2001, 57, 2065.
2. A. G. Brook, A. R. Bassindale in Rearrangements in Ground and Excited States (Ed.:, P. de Mayo), Academic Press, New York, 1980, vol. 2, pp. 149-227.
3. M. A. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.
4. K. Tomooka in The Chemistry of Functional Groups Volume 104: The Chemistry of Organic Lithium Compounds (Eds.:, Z. Rappoport, I. Marek), Wiley-VCH, Chichester, 2004, ch. 12, pp. 749-828 for recent examples of the application of the Brook rearrangement, see
5. C. Wang, Z.-B. Gan, J. Lu, X. Wu, Z.-L. Song, Tetrahedron Lett. 2011, 52, 2462.
6. B. Liu, C.-D. Lu, J. Org. Chem. 2011, 76, 4205.
7. Z. Song, Z. Lei, L. Gao, X. Wu, L. Li, Org. Lett. 2010, 12, 5298.
8. D. C. Schmitt, J. S. Johnson, Org. Lett. 2010, 12, 944.
9. M. Sasaki, H. Ikemoto, K. Takeda, Heterocycles 2009, 78, 2919.
10. A. B. Smith III, W. M. West, Chem. Commun. 2008, 5883.
11. A. B. Smith III, M. O. Duffey, Synlett 2004, 1363.
12. B. M. Comanita, S. Woo, A. G. Fallis, Tetrahedron Lett. 1999, 40, 5283.
13. J. J. Eisch, M. R. Tsai, J. Organomet. Chem. 1982, 225, 5.
14. J. J. Eisch, M. R. Tsai, J. Am. Chem. Soc. 1973, 95, 4065.
15. M. Daney, R. Lapouyade, H. Bouas-Laurent, J. Org. Chem. 1983, 48, 5055.
16. M. Daney, B. Labrande, R. Lapouyade, H. Bouas-Laurent, J. Organomet. Chem. 1978, 159, 385.
17. R. K. Dhar, D. K. Clawson, F. R. Fronczek, P. W. Rabideau, J. Org. Chem. 1992, 57, 2917.
18. M. Harmata, P. Zheng, P. R. Schreiner, A. Navarro-Vázquez, Angew. Chem. Int. Ed. 2006, 45, 1966.
19. M. Harmata, P. Zheng, P. R. Schreiner, A. Navarro-Vázquez, Tetrahedron Lett. 2007, 48, 5919.
20. B. A. Narayanan, W. H. Bunnelle, Tetrahedron Lett. 1987, 28, 6261.
21. S. Kobayashi, Y. Mori, J. S. Fossey, M. M. Salter, Chem. Rev. 2011, 111, 2626.
22. M. T. Robak, M. A. Herbage, J. A. Ellman, Chem. Rev. 2010, 110, 3600.
23. F. Ferreira, C. Botuha, F. Chemla, A. Perez-Luna, Chem. Soc. Rev. 2009, 38, 1162.
24. 29Si NMR analysis.
25. A. H. J. F. de Keijzer, F. J. J. de Kanter, M. Schakel, R. F. Schmitz, G. W. Klumpp, Angew. Chem. Int. Ed. Engl. 1996, 35, 1127.
26. P. F. Hudrlik, D. Dai, A. M. Hudrlik, J. Organomet. Chem. 2006, 691, 1257.
27. Z. Wang, H. Fang, Z. Xi, Tetrahedron Lett. 2005, 46, 499.
28. J. P. Perdew, Y. Wang, Phys. Rev. B 1992, 23, 12947.
29. T. H. Dunning, J. Chem. Phys. 1989, 90, 1007.
30. A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378.
31. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision B.2, Gaussian, Inc., Wallingford, CT, 2009.
32. E. P. A. Couzijn, J. C. Slootweg, A. W. Ehlers, K. Lammertsma, J. Am. Chem. Soc. 2010, 132, 18127.
33. R. R. Holmes, Chem. Rev. 1990, 90, 17.
34. O. Desponds, M. Schlosser, J. Organomet. Chem. 1991, 409, 93.
35. D. W. Boerth, A. Streitwieser Jr., J. Am. Chem. Soc. 1981, 103, 6443.
36. A. Streitwieser Jr., P. J. Scannon, H. M. Niemeyer, J. Am. Chem. Soc. 1972, 94, 7936. for silicon migration rationalized on the basis of differences in carbanion stability, see:, L. Bonnafoux, R. Scopelliti, F. R. Leroux, F. Colobert, Tetrahedron Lett. 2007, 48, 8768.
37. J. J. Eshelby, P. C. Crowley, P. J. Parsons, Synlett 1993, 277.
38. T. Seiser, N. Cramer, Angew. Chem. Int. Ed. 2010, 49, 10163.