Selective synthesis of mono- and distannylpyridines from chloropyridinols via an SRN1 mechanism

Journal of Organometallic Chemistry

Volumn 695, Issue 24, 2010, Pages 2578-2585

  Silbestri, Gustavo F ^a   Lo Fiego, Marcos J ^a   Lockhart, María T ^a   Chopa, Alicia B ^a  

^a UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

Author keywords

(Trimethylstannyl)pyridines; (Trimethylstannyl)sodium; Bis(trimethylstannyl)pyridines; Diethyl chloropyridyl phosphates; S RN1

Indexed keywords

(TRIMETHYLSTANNYL)PYRIDINES; (TRIMETHYLSTANNYL)SODIUM; BIS(TRIMETHYLSTANNYL)PYRIDINES; DIETHYL CHLOROPYRIDYL PHOSPHATES; S RN1;

PHOSPHATES; SODIUM; SYNTHESIS (CHEMICAL);

PYRIDINE;

EID: 77957793636     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.08.032     Document Type: Article

References (39)

1. M. Balabrubramanian, and J.G. Keay A.R. Katrizky, C.W. Rees, E.V.F. Scriven, Comprehensive Heterocyclic Chemistry II vol. 5 1996 Pergamon Press London (Chapter 6, and references cited therein)
2. A.A.-M. Abdel-Aziz Tetrahedron Lett. 48 2007 2861
3. F. Hoffmann-Emery, H. Hilpert, M. Scalone, and P. Waldmeier J. Org. Chem. 71 2006 2000
4. J.-C. Fernández, L. Solé-Feu, D. Fernández-Former, N. de la Figuera, P. Forns, and F. Albericio Tetrahedron Lett. 46 2005 581
5. E.C. Constable Coord. Chem. Rev. 252 2008 842
6. I. Eryazici, C.N. Moorefield, and G.R. Newkome Chem. Rev. 108 2008 1834
7. J. Vicente, J. Gil- Rubio, N. Barquero, P.G. Jones, and D. Bautista Organometallics 27 2008 646
8. G. Burzicki, A.S. Voisin-Chiret, J. Sopkov-de Oliveira Santos, and S. Rault Tetrahedron 65 2009 5413
9. C. Corinne Gosmini, C. Bassene-Ernst, and M. Durandetti Tetrahedron 65 2009 6141
10. H. S-Kim, and R.D. Rieke Tetrahedron Lett. 50 2009 5329
11. J. Barluenga, A. Jimenez-Aquino, M.A. Fernández, F. Aznar, and C. Valdés Tetrahedron 64 2008 778
12. S.J. Teague J. Org. Chem. 73 2008 9765
13. Y. Liu, Q. Ding, and X. Wu J. Org. Chem. 73 2008 6025
14. S. Diring, P. Retailleau, and R.J. Ziessel Org. Chem. 72 2007 10181
15. B.C. Ranu, R. Jana, and S. Sowniah J. Org. Chem. 72 2007 3152 and further references cited therein
16. F. Havas, N. Leygue, M. Danel, B. Mestre, Ch. Galaup, and C. Picard Tetrahedron 65 2009 7673
17. Y.A. Getmanenko, and R.J. Twieg J. Org. Chem. 73 2008 830
18. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174
19. N. Giuseppone, J.-L. Schmitt, and J.-M. Lehn J. Am. Chem. Soc. 128 2006 16748
20. M. Ghirotti, P.F.H. Schwab, M.T. Indelli, C. Chiorboll, and F. Scandola Inorg. Chem. 45 2006 4331
21. Y.D.M. Champouret, R.K. Chaggar, I. Dadhiwala, J. Fawcett, and G.A. Solan Tetrahedron 62 2006 79
22. A.B. Chopa, M.T. Lockhart, and G.F. Silbestri Organometallics 19 2000 2249
23. A.B. Chopa, M.T. Lockhart, and G.F. Silbestri Organometallics 20 2001 3358
24. A.B. Chopa, M.T. Lockhart, and G.F. Silbestri Organometallics 21 2002 5874
25. A.B. Chopa, M.T. Lockhart, and V.B. Dorn Organometallics 21 2002 1425
26. A.B. Chopa, V.B. Dorn, M.A. Badajoz, and M.T. Lockhart J. Org. Chem. 69 2004 3801
27. V.B. Dorn, M.A. Badajoz, M.T. Lockhart, A.B. Chopa, and A.B. Pierini J. Organometal. Chem. 693 2008 2458
28. For reviews see:
29. RN1 mechanism ACS Monograph 178 1983 American Chemical Society Washington, DC
30. R.A. Rossi, A.B. Pierini, and A.N. Santiago L.A. Paquette, R. Bittman, Organic Reactions vol. 54 1999 Wiley & Sons (Chapter 1)
31. R.A. Rossi, A.B. Pierini, and A.B. Peñeñory Chem. Rev. 103 2003 71
32. A.B. Chopa, G.F. Silbestri, and M.T. Lockhart J. Organometal. Chem. 690 2005 3865
33. Previous results showed that different aryl DEP's did not react with organotin anions without photostimulation. See Ref. 6d.
34. E.F. Córsico, and R.A. Rossi Synlett 2000 227
35. Y. Yamamoto, and A. Yanagi Chem. Pharm. Bull. 30 1982 1731
36. M. Gielen, A. Davies, K. Pannell, and E. Tiekink Tin Chemistry: Fundamentals, Frontiers and Applications 2008 Wiley & Sons Chichester
37. T. Sato Comprehensive Organometallic Chemistry II vol. 8 1995 Pergamon New York
38. L.-C. Campeau, and K. Fagnou Chem. Soc. Rev. 36 2007 1058
39. G.W. Kenner, and N.R. Williams J. Chem. Soc. 1955 522