Synthesis, characterization and primary evaluation of the synthetic efficiency of supported vinyltins and allyltins

Journal of Organometallic Chemistry

Volumn 695, Issue 9, 2010, Pages 1414-1424

  Kerric, Gaelle ^a   Grognec, Erwan Le ^a   Fargeas, Valérie ^a   Zammattio, Françoise ^a   Quintard, Jean Paul ^a   Biesemans, Monique ^b   Willem, Rudolph ^b  

^a UNIVERSITÉ DE NANTES   (France)

^b VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Allylstannation; Allyltin; HRMAS NMR; Stille; Vinyltin

Indexed keywords

GRAFTING (CHEMICAL); ORGANOMETALLICS;

ALLYLSTANNATION; ALLYLTIN; HR-MAS NMR; STILLE; VINYLTIN;

TIN COMPOUNDS;

EID: 77950296049     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.01.038     Document Type: Article

References (64)

1. Pereyre M., Quintard J.-P., and Rahm A. Tin in Organic Synthesis (1987), Butterworths, London
2. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442-4489
3. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293
4. Marshall J.A. Chem. Rev. 96 (1996) 31-48
5. Thomas E.J. Chem. Commun. (1997) 411-418
6. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763-2794
7. Thomas E.J. Chem. Rec. 7 (2007) 115-120
8. Marshall J.A. J. Org. Chem. 72 (2007) 8153-8166
9. Chrétien J.-M., Kilburn J.D., Zammattio F., Le Grognec E., and Quintard J.-P. New trends in the synthesis of solid-supported organotin reagents. In: Davies A.G., Gielen M., Pannell K.H., and Tiekink E.R.T. (Eds). Tin Chemistry - Fundamentals Frontiers and Applications (2008), Wiley-Chichester 607-621
10. Gerigk U., Gerlach M., Neumann W.P., Vieler R., and Weintritt V. Synthesis (1990) 448-452
11. Neumann W.P., and Peterseim M. React. Polym. 20 (1993) 189-205
12. Dumartin G., Kharboutli J., Delmond B., Frangin Y., and Pereyre M. Eur. J. Org. Chem. (1999) 781-783
13. Ruel G., Ngo K.T., Dumartin G., Delmond B., and Pereyre M. J. Organomet. Chem. 444 (1993) C18-C20
14. Dumartin G., Pourcel M., Delmond B., Donard O., and Pereyre M. Tetrahedron Lett. 39 (1998) 4663-4666
15. Otera J., Biesemans M., Pinoie V., Poelmans K., and Willem R. Green organotin catalysts. In: Davies G., Gielen M., Pannell K.H., and Tiekink E.R.T. (Eds). Tin Chemistry - Fundamentals Frontiers and Applications (2008), Wiley-Chichester 667-680
16. Poelmans K., Pinoie V., Verbruggen I., Biesemans M., Deshayes G., Duquesne E., Delcourt C., Degée P., Miltner H.E., Dubois P., and Willem R. Organometallics 27 (2008) 1841-1849
17. Camacho-Camacho C., Biesemans M., Van Poeck M., Mercier F.A.G., Willem R., Darriet-Jambert K., Jousseaume B., Toupance T., Schneider U., and Gerigk U. Chem. Eur. J. 11 (2005) 2455-2461
18. Poelmans K., Pinoie V., Verbruggen I., Biesemans M., Van Assche G., Deshayes G., Degée P., Dubois P., and Willem R. Appl. Organomet. Chem. 21 (2007) 504-513
19. Pinoie V., Poelmans K., Miltner H.E., Verbruggen I., Biesemans M., Van Assche G., Van Mele B., Martins J.C., and Willem R. Organometallics 26 (2007) 6718-6725
20. Biesemans M., Mercier F.A.G., Van Poeck M., Martins J., Dumartin G., and Willem R. Eur. J. Inorg. Chem. (2004) 2908-2913
21. Mercier F.A.G., Biesemans M., Altmann R., Willem R., Pintelon R., Schoukens J., Delmond B., and Dumartin G. Organometallics 20 (2001) 958-962
22. Chrétien J.-M., Zammattio F., Le Grognec E., Paris M., Cahingt B., Montavon G., and Quintard J.-P. J. Org. Chem. 70 (2005) 2870-2873
23. Chrétien J.-M., Zammattio F., Gauthier D., Le Grognec E., Paris M., and Quintard J.-P. Chem. Eur. J. 12 (2006) 6816-6828
24. Fraboulet G., Fargeas V., Paris M., Quintard J.-P., and Zammattio F. Tetrahedron 65 (2009) 3953-3960
25. Chrétien J.-M., Mallinger A., Zammattio F., Le Grognec E., Paris M., Montavon G., and Quintard J.-P. Tetrahedron Lett. 48 (2007) 1781-1785
26. Kerric G., Le Grognec E., Zammattio F., Paris M., and Quintard J.-P. J. Organomet. Chem. 695 (2010) 103-110
27. Hernán A.G., Guillot V., Kuvshinov A., and Kilburn J.D. Tetrahedron Lett. 44 (2003) 8601-8603
28. Hernán A.G., Horton P.N., Hursthouse M.B., and Kilburn J.D. J. Organomet. Chem. 691 (2006) 1466-1475
29. Pham P.D., Vitz J., Chamignon C., Martel A., and Legoupy S. Eur. J. Org. Chem. (2009) 3249-3257
30. Carrera N., Gutierrez E., Benavente R., Villavieja M.M., Albeniz A.C., and Espinet P. Chem. Eur. J. 14 (2008) 10141-10148
31. Sherrington D.C. Chem. Commun. (1998) 2275-2286
32. Delmond B., and Dumartin G. In: Gielen M., Willem R., and Wrackmeyer B. (Eds). Solid State Organometallic Chemistry: Methods and Applications (1999), John Wiley & Sons, Chichester 445-471
33. Parrain J.-L., Duchêne A., and Quintard J.-P. J. Chem. Soc., Perkin Trans. 1 (1990) 187-189
34. Parrain J.-L., Duchêne A., and Quintard J.-P. Tetrahedron Lett. 31 (1990) 1857-1860
35. Launay V., Beaudet I., and Quintard J.-P. Bull. Soc. Chim. Fr. 134 (1997) 937-946
36. Parrain J.-L., Beaudet I., Duchêne A., Watrelot S., and Quintard J.-P. Tetrahedron Lett. 34 (1993) 5445-5448
37. Martins J.C., Mercier F.A.G., Vandervelden A., Biesemans M., Wieruszeski J.-M., Humpfer E., Willem R., and Lippens G. Chem. Eur. J. 8 (2002) 3431-3441
38. Deshayes G., Poelmans K., Verbruggen I., Camacho-Camacho C., Degée P., Pinoie V., Martins J.C., Piotto M., Biesemans M., Willem R., and Dubois P. Chem. Eur. J. 11 (2005) 4552-4561
39. M. Biesemans, R. Willem, Multidimensional NMR in organotin chemistry and catalysis, in: R.K. Harris, R. Wasylishen (Eds.), Encyclopedia of Magnetic Resonance, John Wiley, Chichester. doi: 10.1002/9780470034590.emrstm1079.
40. .
41. Laatikainen R., Niemitz M., Malaisse W.J., Biesemans M., and Willem R. Magn. Reson. Med. 36 (1996) 359-365
42. Launay V., Beaudet I., and Quintard J.-P. Synlett (1997) 821-823
43. Fargeas V., Zammattio F., Chrétien J.-M., Bertrand M.-J., Paris M., and Quintard J.-P. Eur. J. Org. Chem. (2008) 1681-1688
44. Matarasso-Tchiroukhine E., and Cadiot P. J. Organomet. Chem. 121 (1976) 155-168
45. Aoki S., Mikami K., Terada M., and Nakai T. Tetrahedron 49 (1993) 1783-1792
46. Balduzzi S., Brook M.A., and McGlinchey M.J. Organometallics 24 (2005) 2617-2627
47. Dumartin G., Quintard J.-P., and Pereyre M. J. Organomet. Chem. 185 (1980) C34-C36
48. Wickham G., Young D., and Kitching W. J. Org. Chem. 47 (1982) 4884-4895
49. Quintard J.-P., Degueil-Castaing M., Dumartin G., Rahm A., and Pereyre M. J. Chem. Soc., Chem. Commun. (1980) 1004-1005
50. Pereyre M., Quintard J.-P., and Rahm A. Pure Appl. Chem. 54 (1982) 29-41
51. Quintard J.-P., Degueil-Castaing M., Dumartin G., Barbe B., and Petraud M. J. Organomet. Chem. 234 (1982) 27-40
52. G. Dumartin, Phd thesis, 1987, University of Bordeaux 1.
53. Watrelot S., Parrain J.-L., and Quintard J.-P. J. Org. Chem. 59 (1994) 7959-7961
54. Fliegel F., Beaudet I., Watrelot-Bourdeau S., Cornet N., and Quintard J.-P. J. Organomet. Chem. 690 (2005) 659-673
55. Pate F., Duguet N., Oulyadi H., Harrison-Marchand A., Fressigné C., Valnot J.-Y., Lasne M.-C., and Maddaluno J. J. Org. Chem. 72 (2007) 6982-6991
56. Piller F.M., Metzger A., Schade M.A., Haag B.A., Gavryushin A., and Knochel P. Chem. Eur. J. 15 (2009) 7192-7202
57. Lipshutz B.H., and James B. J. Org. Chem. 59 (1994) 7585-7587
58. Henze W., Vyater A., Krause N., and Gschwind R.M. J. Am. Chem. Soc. 127 (2005) 17335-17342
59. Snyder J.P., and Bertz S.H. J. Org. Chem. 60 (1995) 4312-4313
60. Watrelot-Bourdeau S., Parrain J.-L., and Quintard J.-P. J. Org. Chem. 62 (1997) 8261-8263
61. Mason J. Multinuclear NMR (1987), Plenum Press, New York p. 627
62. Roush W.R., Ando K., Powers D.B., Palkowitz A.D., and Halterman R.L. J. Am. Chem. Soc. 112 (1990) 6339-6348
63. Nokami J., Yoshizane K., Matsuura H., and Sumida S.-I. J. Am. Chem. Soc. 120 (1998) 6609-6610
64. Li G.-L., and Zhao G. J. Org. Chem. 70 (2005) 4272-4278