Batch stille coupling with insoluble and recyclable stannylated polynorbornenes

Advanced Synthesis and Catalysis

Volumn 354, Issue 18, 2012, Pages 3551-3560

  Martínez Arranz, Sheila ^a   Carrera, Nora ^a   Albéniz, Ana C ^a   Espinet, Pablo ^a   Vidal Moya, Alejandro ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b INSTITUTO DE TECNOLOGÍA QUÍMICA   (Spain)

Author keywords

C C coupling; green chemistry; polymers; recycling; Stille reaction; tin

Indexed keywords

EID: 84871083066     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200624     Document Type: Review

References (59)

1. V. Farina, V. Krishanamurthy, W. J. Scott, The Stille Reaction, Wiley, New York, 1998
2. P. Espinet, M. Genov, in: Tin Chemistry: Fundamentals, Frontiers and Applications, (Eds. , A. G. Davies, M. Gielen, K. H. Pannell, R. T. Tiekink,), Wiley, Chichester, 2008, pp 561-578
3. P. Espinet, A. Echavarren, Angew. Chem. 2004, 116, 4808-4839
4. Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
5. Recent examples of Stille couplings, some of them applied to natural product synthesis and polymer preparation
6. S. S. Scully, J. A. Porco Jr, Angew. Chem. 2011, 123, 9896-9900
7. Angew Chem. Int. Ed. 2011, 50, 9722-9726
8. B. Carsten, F. He, H. J. Son, T. Xu, L. Yu, Chem. Rev. 2011, 111, 1493-1528
9. S. Lu, Z. Xu, M. Bao, Y. Yamamoto, Angew. Chem. 2008, 120, 4438-4441
10. Angew. Chem. Int. Ed. 2008, 47, 4366-4369
11. J. Li, M. Lutz, A. L. Spek, G. P. M. van Klink, G. van Koten, R. J. M. Klein Gebbink, Organometallics 2010, 29, 1379-1387
12. H. W Lam, G. Pattenden, Angew. Chem. 2002, 114, 526-529
13. Angew. Chem. Int. Ed. 2002, 41, 508-511.
14. Different methodologies have been used to tackle the problem of the separation of toxic tin by-products, including the use of monoorganotin reagents
15. D. A. Powell, T. Maki, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 510-511
16. A. Herve, A. L. Rodriguez, E. Fouquet, J. Org. Chem. 2005, 70, 1953-1956
17. S. Liu, T. Fukuyama, M. Sato, I. Ryu, Synlett 2004, 1814-1816
18. C. Chiappe, G. Imperato, E. Napolitano, D. Pieraccini, Green Chem. 2004, 6, 33-36; catalytic amounts of the tin reagent
19. W. P. Gallagher, R. Maleczka Jr, J. Org. Chem. 2005, 70, 841-846
20. W. P. Gallagher, I. Terstiege, R. E. Maleczka Jr, J. Am. Chem. Soc. 2001, 123, 3194-3204; fluorinated alkyl substituents
21. K. Olofsson, S.-Y. Kim, M. Larhed, D. P. Curran, A. Hallberg, J. Org. Chem. 1999, 64, 4539-4541; a polyaromatic hydrocarbon substituent
22. D. Stien, S. Gastaldi, J. Org. Chem. 2004, 69, 4464-4470, and the conventional elimination of tributyltin halides as tributyltin fluorides
23. J. E. Leibner, J. Jacobus, J. Org. Chem. 1979, 44, 449-450
24. D. C. Harrowven, I. L. Guy, Chem. Commun. 2004, 67, 1968-1969
25. D. C. Harrowven, D. P. Curran, S. L. Kostiuk, I. L. Wallis-Gay, S. Whiting, K. J. Stenning, B. Tang, E. Packard, L. Nanson, Chem. Commun. 2010, 46, 6335-6337.
26. N. Carrera, A. C. Albéniz, Eur. J. Inorg. Chem. 2011, 2347-2360.
27. G. Kerric, E. Le Grognec, F. Zammattio, M. Paris, J-P. Quintard, J. Organomet. Chem. 2010, 695, 103-110
28. J.-M. Chrétien, A. Mallinger, F. Zammattio, E. Le Grognec, M. Paris, G. Montavon, J.-P. Quintard, Tetrahedron Lett. 2007, 48, 1781-1785
29. K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677
30. Angew. Chem. Int. Ed. 1998, 37, 2534 -2537
31. H. Kuhn, W. P. Neumann, Synlett 1994, 123-124.
32. I. Meana, A. C. Albéniz, P. Espinet, Adv. Synth. Catal. 2010, 352, 2887-2891
33. N. Carrera, E. Gutierrez, R. Benavente, M. M. Villavieja, A. C. Albéniz, P. Espinet, Chem. Eur. J. 2008, 14, 10141-10148.
34. N. Carrera, A. Salinas-Castillo, A. C. Albéniz, P. Espinet, R. Mallavía, J. Organomet. Chem. 2011, 696, 3316-3321.
35. N. Louaisil, P. D. Pham, F. Boeda, D. Faye, A.-S. Castanet, S. Legoupy, Eur. J. Org. Chem. 2011, 143-149
36. P. D. Pham, J. Vitz, C. Chamignon, A. Martel, S. Legoupy, Eur. J. Org. Chem. 2009, 3249-3257
37. J. Vitz, D. H. Mac, S. Legoupy, Green Chem. 2007, 9, 431-433.
38. S. Martínez-Arranz, A. C. Albéniz, P. Espinet, Macromolecules 2010, 43, 7482-7487.
39. D. C. White, Microchim. Acta 1961, 49, 449-456.
40. J. A. Casares, P. Espinet, J. M. Martín-Álvarez, J. M. Martínez de Ilarduya, G. Salas, Eur. J. Inorg. Chem. 2005, 3825-3831.
41. P. P. Chu, W. J. Huang, F. C. Chang S. Y. Fan, Polymer, 2000, 401-404.
42. W. Kaminsky, A. Bark, M. Arndt, Makromol. Chem. Macromol. Symp. 1991, 41, 83-93.
43. M. Arndt, R. Engehausen, W. Kaminsky, K. Zoumis, J. Mol. Catal. A: Chem. 1995, 101, 171-178.
44. N. Carrera, M. H. Pérez-Temprano, A. C. Albéniz, J. A. Casares, P. Espinet, Organometallics 2009, 28, 3957-3958.
45. E. A. Hill, K. Hsieh, K. Condroski, H. Sonnentag, D. Skalitzky, D. Gagas, J. Org. Chem. 1989, 54, 5286-5292.
46. Y. Tatsuno, T. Yoshida, S. Otsuka, in: Inorganic Syntheses, (Ed.:, D. F. Shriver,), Wiley-Interscience, New York, 1979, Vol. 19, pp 220- 221.
47. R. Usón, J. Foniés, J. A. Nalda, M. J. Lozano, P. Espinet, A. C. Albéniz, Inorg. Chim. Acta 1989, 156, 251-256.
48. A. C. Albéniz, P. Espinet, R. López Fernández, Organometallics 2003, 22, 4206-4212.
49. D. R. Coulson, L. C. Satek, S. O. Grim, Inorg. Synth. 1990, 28, 107-109.
50. CAS registry number: 2143-90-0., A. M. Echavarren, J. K. Stille, J. Am. Chem. Soc. 1987, 109, 5478-5486.
51. CAS registry number: 140-67-0.
52. P. Gomes, C. Gosmini, J. Périchon, J. Org. Chem. 2003, 68, 1142-1145
53. R. C. Haley, J. A. Miller, H. C. S. Wood, J. Chem. Soc. C 1969, 264-268.
54. CAS registry number: 51207-29-5., Q.-Y. Chen, Z.-T. Li, J. Org. Chem. 1993, 58, 2599-2604.
55. CAS registry number: 613-37-6., H. A. Stefani, J. M. Pena, F. Manarin, R. A. Ando, D. M. Leal, N. Petragnani, Tetrahedron Lett. 2011, 52, 4398-4401.
56. CAS registry number: 10355-12-1., S. E. Denmark, R. C. Smith, S. A. Tymonko, Tetrahedron 2007, 63, 5730-5738.
57. CAS registry number: 17171-17-4., P. Leowanawat, N. Zhang, A.-M Resmerita, B. M. Rosen, V. Percec, J. Org. Chem. 2011, 76, 9946-9955.
58. CAS registry number: 611-94-9., S. S. Kulp, M. J. McGee, J. Org. Chem. 1983, 48, 4097-4098.
59. CAS registry number: 300-57-2., R. Matsubara, A. C. Gutierrez, T. F. Jamison, J. Am. Chem. Soc. 2011, 133, 19020-19023.