Preparation of tertiary benzylic nitriles from aryl fluorides [1]

Journal of the American Chemical Society

Volumn 122, Issue 4, 2000, Pages 712-713

  Caron, Stéphane ^a   Vazquez, Enrique ^a   Wojcik, Jill M ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; NITRILE;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LETTER; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0033950371     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9933846     Document Type: Letter

References (28)

1. Zoltewicz, J. A. Top. Curr. Chem. 1975, 59, 33-64.
2. March, J. In Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons: New York, 1985; pp 576-607.
3. Broxton, T. J.; Muir, D. M.; Parker, A. J. J. Org. Chem. 1975, 40, 3230-3233.
4. Vaslow, V. M. J. Fluorine Chem. 1993, 61, 193-216.
5. Loupy, A.; Philippon, N.; Pigeon, P.; Sansoulet, J.; Galons, H. Synth. Commun. 1990, 20, 2855-2864.
6. Sommer, M. B.; Begtrup, M.; Bogeso, K. P. J. Org. Chem. 1990, 55, 4817-4821.
7. Zhang, X.-M.; Yang, D.-L; Liu, Y.-C. J. Org. Chem. 1993, 58, 224-227.
8. Makosza, M.; Podraza, R.; Kwast, A. J. Org. Chem. 1994, 59, 6796-6799.
9. Plevey, R. G.; Sampson, P. J. Chem. Soc., Perkin Trans. 1 1987, 2129-2136.
10. Rose-Munch, F.; Aniss, K.; Rose, E. J. Organomet. Chem. 1990, 385, C1-C3.
11. Mannhold, R. In Recent Advances in Receptor Chemistry; Melchiorre, C., Giannella, M., Eds.; Elsevier Science Publishers: Amsterdam, 1988; p 147.
12. Dei, S.; Romanelli, M. N.; Scapecchi, S.; Teodori, E.; Chiarini, A.; Gualtieri, F. J. Med. Chem. 1991, 34, 2219-2225.
13. Mitani, K.; Sakurai, S.; Suzuki, T.; Morikawa, E.; Kato, H.; Ito, Y.; Fujita, T. Chem. Pharm. Bull. 1988, 36, 4121-4135.
14. Christensen, S. B.; Guider, A.; Forster, C. J.; Gleason, J. G.; Bender, P. E.; Karpinski, J. M.; DeWolf, W. E., Jr.; Barnette, M. S.; Underwood, D. C.; Griswold, D. E.; Cieslinski, L. B.; Burman, M.; Bochnowicz, S.; Osborn, R. R.; Manning, C. D.; Grous, M.; Hillegas, L. M.; O'Leary Bartus, J.; Ryan, M. D.; Eggleston, D. S.; Haltiwanger, R. C.; Torphy, T. J. J. Med. Chem. 1998, 41, 821-835.
15. Theodore, L. J.; Nelson, W. L. J. Org. Chem. 1987, 52, 1309-1315.
16. Convery, M. A.; Davis, A. P.; Dunne, C. J.; MacKinnon, J. W. Tetrahedron Lett. 1995, 36, 4279-4282.
17. Tiecco, M.; Testaferri, L.; Tingoli, M.; Bartoli, D. Tetrahedron 1990, 46, 7139-7150.
18. Trivedi, B. K.; Holmes, A.; Stoeber, T. L.; Blankey, C. J.; Roark, W. H.; Picard, J. A.; Shaw, M. K.; Essenburg, A. D.; Stanfield, R. L.; Krause, B. R. J. Med. Chem. 1993, 36, 3300-3307.
19. Okatani, T.; Koyama, J.; Tagahara, K. Heterocycles 1989, 29, 1809-1814.
20. Chelucci, G.; Giocomeli, G.; Scano, G. Gazz. Chim. Ital. 1991, 121, 107-108.
21. Pascal, C.; Dubois, J.; Guénard, D.; Tchertanov, L.; Thoret, S.; Guéritte, F. Tetrahedron 1998, 54, 14737-14756.
22. Chavan, S. P.; Ravindranathan, T.; Patil, S. S.; Dhondge, V. D.; Dantale, S. W. Tetrahedron Lett. 1996, 37, 2629-2630.
23. Leader, H.; Smejkal, R. M.; Payne, C. S.; Padilla, F. N.; Doctor, B. P.; Gordon, R. K.; Chiang, P. K. J. Med. Chem. 1989, 32, 1522-1528.
24. Bush, E. J.; Jones, D. W. J. Chem. Soc., Perkin Trans. 1 1997, 3531-3536.
25. Breukelman, S. P.; Meakins, G. D.; Roe, A. M. J. Chem. Soc., Perkin Trans. 1 1985, 1627-1635.
26. Stevens, R. V. Acc. Chem. Res. 1977, 10, 193-198.
27. We also demonstrated that the alkylation of nitrile 2c with benzyl bromide using KHMDS in toluene also proceeds from the exo face, and the stereochemistry of the product was confirmed using several NMR experiments.
28. The author has deposited atomic coordinates for structures 3n and 3o with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.