Efficient palladium-catalyzed synthesis of aminopyridyl phosphonates from bromopyridines and diethyl phosphite

Synthesis

Volumn , Issue 10, 2008, Pages 1575-1579

  Bessmertnykh, Alla ^a   Douaihy, Christiane Morkos ^a   Muniappan, Sankar ^a   Guilard, Roger ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Catalysis; Cross coupling; Palladium; Phosphonates; Pyridyl halides

Indexed keywords

BROMINE COMPOUNDS; PALLADIUM;

CATALYZED SYNTHESIS; GENERAL METHOD; PALLADIUM CATALYSTS; PHOSPHONATES; TRIETHYLAMINE (TEA);

NANOSTRUCTURED MATERIALS;

AMINOPYRIDYL PHOSPHONATE; BROMOPYRIDINE; DIETHYLPHOSPHITE; PALLADIUM; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; SYNTHESIS;

EID: 44949243960     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072570     Document Type: Article

References (31)

1. For reviews, see: (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
2. (b) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1; Negishi, E.-I., Ed.; Wiley-Interscience: New York, 2002.
3. (c) Beletskaya, I. P. Pure Appl. Chem. 1997, 69, 471.
4. (a) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Synthesis 1981, 56.
5. (b) Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
6. (c) Petrakis, K. S.; Nagabhushan, T. L. J. Am. Chem. Soc. 1987, 109, 2831.
7. (d) Kabachnik, M. M.; Solntseva, M. D.; Izmer, V. V.; Novikova, Z. S.; Beletskaya, I. P. Russ. J. Org. Chem. 1998, 34, 93.
8. (e) Defacqz, N.; de Bueger, B.; Touillaux, R.; Cordi, A.; Marchand-Brynaert, J. Synthesis 1999, 1368.
9. (f) Ngo, H. L.; Lin, W. J. Am. Chem. Soc. 2002, 124, 14298.
10. For Ni- or Cu-mediated coupling of aryl halides with trialkyl phosphites, see: (a) Tavs, P.; Korte, F. Tetrahedron 1967, 23, 4677.
11. (b) Tavs, P. Chem. Ber. 1970, 103, 2428.
12. (c) Osuka, A.; Ohmasa, N.; Yoshida, Y.; Suzuki, H. Synthesis 1983, 69.
13. (d) Yuan, C.; Feng, H. Synthesis 1990, 140.
14. (e) Czech, B. P.; Desai, D. H.; Koszuk, J.; Czech, A.; Babb, D. A.; Robison, T. W.; Bartsch, R. A. J. Heterocycl. Chem. 1992, 29, 867.
15. (f) For Cu-promoted coupling of aryl halides with dialkyl phosphites, see: Ogawa, T.; Usuki, N.; Ono, N. J. Chem. Soc., Perkin Trans. 1 1998, 2953.
16. (g) For Cu-catalyzed coupling of aryl iodides with dialkyl phosphites, see: Gelman, D.; Jiang, L.; Buchwald, S. L. Org. Lett. 2003, 5, 2315.
17. 3, see: Freedman, L. D.; Doak, G. O. J. Am. Chem. Soc. 1955, 77, 173.
18. (i) For Friedel-Crafts reaction of arenes with phosphorous derivatives, see: Kosolapoff, G. M. J. Am. Chem. Soc. 1952, 74, 4119.
19. (j) For nucleophilic substitution reaction of activated aryl halides with sodium dialkylphosphites, see: Boumekouez, A.; About-Jaudet, E.; Savignac, N. C. P. J. Organomet. Chem. 1992, 440, 297.
20. RN1 substitution reaction of aryl halides with sodium dialkylphosphites, see: Beugelmans, R.; Chbani, M. Bull. Soc. Chim. Fr. 1995, 132, 290.
21. (a) Johansson, T.; Stawinski, J. Chem. Commun. 2001, 2564.
22. (b) Ayyappan, P.; Evans, O. R.; Foxman, B. M.; Wheeler, K. A.; Warren, T. H.; Lin, W. Inorg. Chem. 2001, 40, 5954.
23. (c) Ayyappan, P.; Evans, O. R.; Cui, Y.; Wheeler, K. A.; Lin, W. Inorg. Chem. 2002, 41, 4978.
24. (d) Ziessel, R. F.; Charbonniere, L. J.; Mameri, S.; Camerel, F. J. Org. Chem. 2005, 14, 9835.
25. Bulot, J. J.; Aboujaoude, E. E.; Collignon, N.; Savignac, P. Phosphorus, Sulfur Relat. Elem. 1984, 21, 197.
26. Penicaud, V.; Odobel, F.; Bujoli, B. Tetrahedron Lett. 1998, 39, 3689.
27. (a) Yates, F. S. Pyridines and their Benzo Derivatives: (vi) Applications, In Comprehensive Heterocyclic Chemistry. The Structure, Reactions, Synthesis and Uses of Heterocyclic Compounds, Vol. 2; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984.
28. (b) Pyridine and its Derivatives, Part 5; Newkome, G. R., Ed.; Wiley-Interscience: New York, 1984.
29. (c) The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals; Merck Research Laboratories Division of Merck & CO., INC.: Whitehouse Station NJ, 2001.
30. Pierrat, P.; Gros, P. C.; Fort, Y. J. Comb. Chem. 2005, 7, 879.
31. Gooßen, L. J.; Dezfuli, M. K. Synlett 2005, 445.