Noncryogenic I/Br-Mg exchange of aromatic halides bearing sensitive functional groups using i-PrMgCl-Bis[2-(N,N-dimethylamino)ethyl] ether complexes

Organic Letters

Volumn 8, Issue 2, 2006, Pages 305-307

  Wang, Xiao Jun ^a   Sun, Xiufeng ^a   Zhang, Li ^a   Xu, Yibo ^a   Krishnamurthy, Dhileepkumar ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544454968     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052704p     Document Type: Article

References (20)

1. For a review, see: Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302.
2. (a) Knochel, P.; Krasovskiy, A. Angew. Chem., Int. Ed. 2004, 43, 3333.
3. (b) Yang, X.; Rotter, T.; Piazza, C.; Knochel, P. Org. Lett. 2003, 5, 1229.
4. (c) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottlander, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618.
5. For example, see: (a) Boymond, L.; Rottländer, M.; Cahiez, G.; Knochel, P.; Krasovskiy, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1701.
6. (b) Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565.
7. (c) Varchi, G.; Ricci, A.; Cahiez, G.; Knochel, P. Tetrahedron 2000, 56, 2727.
8. Wang, X.-j.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2005, 7, 5593.
9. Uhm, H. L. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; p 117.
10. For synthetic applications of boronic acids, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
11. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
12. (c) Suzuki, A. Pure Appl. Chem. 1994, 66, 213.
13. (d) Suzuki, A. Pure Appl. Chem. 1991, 63, 419.
14. (a) Sapountzis, I.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 1610.
15. (b) Kneisel, F. F.; Knochel, P. Synlett 2002, 11, 1799.
16. Varchi, G.; Kofink, C.; Lindsay, D. M.; Ricci, A.; Knochel, P. Chem. Commun. 2003, 396.
17. 7a
18. Vu, V. A.; Bérillon, L.; Knochel, P. Tetrahedron Lett. 2001, 42, 6847.
19. Preliminary experiments indicated that TMEDA as an alternative ligand was less effective for this exchange, and N-methylmorpholine had no effect at all.
20. 4 and concentrated. The residue was purified by crystallization in hexane to give 3c (187 mg, 89%).