Removal, recovery, and recycling of triarylphosphonium-supported tin reagents for various organic transformations

Organic Letters

Volumn 9, Issue 18, 2007, Pages 3591-3594

  Poupon, Jean Christophe ^a   Marcoux, David ^a   Cloarec, Jean Manuel ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548543459     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701447q     Document Type: Article

References (58)

1. (a) Neumann, W. P. Synthesis 1987, 665.
2. (b) Curran, D. P. Synthesis 1988, 417.
3. (c) Curran, D. P. Synthesis 1988, 489.
4. (d) Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
5. (e) Organotin Chemistry, 2nd ed.; Davies, A. L., Ed.; Wiley-VCH: Weinheim, New York, 2004.
6. Thoonen, S. H. L.; Deelman, B. J.; van Koten, G. J. Organomet. Chem. 2004, 689, 2145.
7. Several approaches have been reported to remove tin hydride residues from reaction mixtures: (a) Berge, J. M.; Roberts, S. M. Synthesis 1979, 471.
8. (b) Leibner, J. E.; Jacobus, J. J. Org. Chem. 1979, 44,449.
9. (c) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
10. (d) Farina, V. J. Org. Chem. 1991, 56, 4985.
11. (e) Crich, D.; Sun, S. X. J. Org. Chem. 1996, 61, 7200.
12. (f) Renaud, P.; Lacote, E.; Quaranta, L. Tetrahedron Lett. 1998, 39, 2123.
13. (g) Edelson, B. S.; Stoltz, B. M.; Corey, E. J. Tetrahedron Lett. 1999, 40, 6729.
14. (h) Salomon, C. J.; Danelon, G. O.; Mascaretti, O. A. J. Org. Chem. 2000, 65, 9220.
15. For a discussion of this issue, see: (a) Baguley, P. A.; Walton, J. C. Angew. Chem., Int. Ed. 1998, 37, 3073.
16. (b) Studer, A.; Amrein, S. Synthesis 2002, 835.
17. (a) Poupon, J. C; Boezio, A. A.; Charette, A. B. Angew. Chem., Int. Ed. 2006, 45, 1415.
18. (b) Zoute, L.; Lacombe, C.; Quirion, J. C.; Charette, A. B.; Jubault, P. Tetrahedron Lett. 2006, 47, 7931.
19. For reviews on soluble supports: (a) Chen, J. N.; Yang, G. C.; Zhang, H. Q.; Chen, Z. X. React. Funct. Polym. 2006, 66, 1434.
20. (b) Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325.
21. Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.
22. For pioneering work on removal of tin reagents, see: (a) Light, J.; Breslow, R. Tetrahedron Lett. 1990, 31, 2957.
23. (b) Clive, D. L. J.; Yang, W. J. Org. Chem. 1995, 60, 2607.
24. For solid supported tin reagents: (a) Neumann, W. P.; Peterseim, M. React. Polym. 1993, 20, 189.
25. (b) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R.; Weintritt, V. Synthesis 1990,448.
26. (c) Kuhn, H.; Neumann, W. P. Synlett 1994, 123.
27. (d) Gerlach, M.; Jordens, F.; Kuhn, H.; Neumann, W. P.; Peterseim, M. J. Org. Chem. 1991, 56, 5971.
28. (e) Neumann, W. P.; Peterseim, M. Synlett 1992, 801.
29. (f) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem.. Int. Ed. 1998, 37, 2534.
30. (g) Hernan, A. G.; Kilburn, J. D. Tetrahedron Lett. 2004, 45, 831.
31. (h) Hernán, A. G.; Guillot, V.; Kuvshinov, A.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 8601.
32. (i) Chrétien, J. M.; Zammattio, F.; Le Grognec, E.; Paris, M.; Cahingt, B.; Montavon, G.; Quintard, J. P. J. Org. Chem. 2005, 70, 2870.
33. (j) Chrétien, J. M.; Zammattio, F.; Gauthier, D.; Le Grognec, E.; Paris, M.; Quintard, J. P. Chem.-Eur. J. 2006, 12, 6816.
34. (k) Chrétien, J. M.; Mallinger, A.; Zammattio, F.; Le Grognec, E.; Paris, M.; Montavon, G.; Quintard, J. P. Tetrahedron Lett. 2007, 48, 1781.
35. (l) Chemin, A.; Deleuze, H.; Maillard, B. J. Chem. Soc., Perkin Trans. 1999, 1, 137.
36. (a) Enholm, E. J.; Gallagher, M. E.; Moran, K. M.; Lombardi, J. S.; Schulte, J. P. Org. Lett. 1999, 1, 689.
37. (b) Enholm, E. J.; Schulte, J. P. Org. Lett. 1999, 1, 1275.
38. Curran, D. P.; Hadida, S.; Kim, S. Y.; Luo, Z. Y. J. Am. Chem. Soc 1999, 121, 6607.
39. 2 solution upon ether addition (ca. ≤5:1 v/v). With reagent 2 and 3, hexanes had to be used in significant amounts (ca. 9:1 v/v).
40. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. (NY.) 1997, 50, 1.
41. (b) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
42. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
43. Analysis by ICP-AES of the product indicated that the concentration in residual tin of the final product was 13 ppm (crude) and <5 ppm (after flash chromatography).
44. See Supporting Information for typical crude NMR spectra and further experimental details.
45. (a) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554.
46. (b) Stork, G.; Sher, P. M. J. Am. Chem. Soc 1986, 108, 303.
47. 2 containing traces of BHT.
48. Horner, L.; Mummenthey, G.; Moses, H.; Beck, P. Chem. Ber. 1966, 99, 2782.
49. Fu, Q. J.; Steele, A. M.; Tsang, S. C. Green Chem. 2001, 3, 71.
50. Analysis by ICP-AES of the crude product indicated that the concentration in residual tin of the final product was 5 ppm (crude).
51. (a) Naruta, Y.; Ushida, S.; Maruyama, K. Chem. Lett. 1979, 919.
52. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
53. For supported allyltin reagents, see: (a) Ref 8a. (b) Ref 7j.
54. (c) Cossy, J.; Rasamison, C.; Pardo, D. G.; Marshall, J. A. Synlett 2001, 629.
55. (d) Cossy, J.; Rasamison, C.; Pardo, D. G. J. Org. Chem. 2001, 66, 7195.
56. (e) Gastaldi, S.; Stien, D. Tetrahedron Lett. 2002, 43, 4309.
57. (f) Stien, D.; Gastaldi, S. J. Org. Chem. 2004, 69, 4464.
58. Analysis by ICP-AES of the crude product indicated that the concentration in residual tin of the final product was 7 ppm.