Preparation of functionalized alkylmagnesium derivatives using an I/Mg-exchange

Organic Letters

Volumn 10, Issue 6, 2008, Pages 1187-1189

  Rauhut, Christian B ^a   Vu, Viet Anh ^b   Fleming, Fraser F ^b   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b DUQUESNE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 56749172466     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8000987     Document Type: Article

References (28)

1. (a) Knochel, P. In Handbook of Functionalized Organometallics; Wiley-VCH, 2005.
2. (b) Boudier, A.; Bromm L. O.; Lotz, M.; Knochel P. Angew. Chem., Int. Ed. 2000, 39, 4415.
3. (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
4. (b) Liu, C.; Ren, H.; Knochel, P. Org. Lett. 2006, 8, 614.
5. (c) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333.
6. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 775, 4438.
7. Fleming, F. F.; Subrahmanyan, G.; Vu, V. A.; Mycka, R. J.; Knochel, P. Org. Lett. 2007, 9, 4507.
8. Hoffmann, R. W.; Kusche, A. Chem. Ber. 1994, 127, 1311.
9. For the preparation of the iodides in most cases the corresponding alcohols were used: (a) Nicolaou, K. C.; Dai, W. M. J. Am. Chem. Soc. 1992, 114, 3908.
10. (b) Plieninger, H.; Zeltner, M. Chem. Ber. 1987, 108, 3286.
11. (c) Riehs, G.; Urban, E. Tetrahedron 1996, 52, 1221; Rocca, P. Tetrahedron 1998, 54, 8771.
12. (d) Brocard, J. Annal. Chim. 1972, 7, 387.
13. (e) Eisch, J. J.; Csaba, A. K.; Chobe, P.; Boleslawski, M. P. J. Org. Chem. 1987, 5, 4427. For more details, see Supporting Information.
14. Krasovskiy, A.; Straub, B.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 159.
15. The formation of cyclopentane was proven by preparing 3-phenyl-pentyl-1, 5-dimagnesium chloride. Its reaction with the alkyl iodide 2b provides the cyclisation product (cyclopentylbenzeue), which was detected by GC-MS as the main product. See also: Yang, X.; Knochel, P. Synlett 2004, 82.
16. Kozikowski. A. P.; Anes, A.; Wetter, H. J. Organomet. Chem. 1978, 3, 164.
17. Pasquinet, E.; Rocca, P.; Godard, A.; Marsais, F.; Quéguiner, G. J. Chem. Soc., Perkin Trans, 1 1998, 3807.
18. (a) Villieras, J.; Rambaud, M. Synthesis 1982, 11, 924.
19. (b) Villieras, J.; Rambaud, M. Org. Synth. 1988, 66, 220.
20. Knochel, P.; Yell, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
21. Treves. G. R.; Stange, H.; Olofson, R. A. J. Am. Chem. Soc. 1967, 89, 6257.
22. (a) Nuhrich, A.; Moulines, J. Tetrahedron 1991, 47, 3075.
23. (b) Clive, D. L. J.; Pham, M. P.; Subedi, R. J. Am. Chem. Soc. 2007, 129, 2713.
24. Ashby, E. C.; Park, B.; Patil, G. S.; Gadru, K.; Guramurthy, R. J. Org. Chem. 1993, 58, 424; Juaristi. E.; Jimbnez-Vizquez, H. A. J. Org. Chem. 1991, 56, 1623; Fehr, C.; Galindo, J. Helv. Chim. Acta 1986, 69, 228.
25. These type of cyclopropane derivatives were obtained by reacting metallic sodium, the chloro derivatives of type 8 and TMSC1: Ruehlmann, K. Synthesis 1971, 236. See also:
26. (a) Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1983, 105, 651.
27. (b) Nakamura E.; Shimada, J.-I; Kuwajima, I. Organometallics 1985, 4. 641.
28. (c) Reissig, H.-U.; Holzinger, H.; Glomsda, G. Tetrahedron 1989, 45, 3139.