Radical copolymerization of a phosphaalkene with styrene: New phosphine-containing macromolecules and their use in polymer-supported catalysis

Angewandte Chemie - International Edition

Volumn 43, Issue 42, 2004, Pages 5682-5685

  Tsang, Chi Wing ^a   Baharloo, Baharnaz ^a   Riendl, David ^a   Yam, Mandy ^a   Gates, Derek P ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Homogeneous catalysis; Inorganic polymers; Multiple bonds; Phosphaalkenes; Phosphanes

Indexed keywords

CATALYSIS; COPOLYMERIZATION; FREE RADICALS; MACROMOLECULES; MONOMERS;

MONOMER RATIOS; RADICAL COPOLYMERIZATION;

STYRENE;

ALKENE DERIVATIVE; AZO COMPOUND; CYANIDE; CYCLOHEXANE DERIVATIVE; MONOMER; PALLADIUM; PHOSPHINE DERIVATIVE; PHOSPHORUS DERIVATIVE; POLYMER; RADICAL; STYRENE;

ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; HYBRID; MACROMOLECULE; POLYMERIZATION; REACTION ANALYSIS; SUZUKI REACTION;

EID: 8444230920     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460939     Document Type: Article

References (66)

1. G. Becker, Z. Anorg. Allg. Chem. 1976, 423, 242.
2. K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy, Wiley, New York, 1998.
3. For general reviews of phosphaalkenes, see: a) F. Mathey, Angew. Chem. 2003, 115, 1616; Angew. Chem. Int. Ed. 2003, 42, 1578;
4. For general reviews of phosphaalkenes, see: a) F. Mathey, Angew. Chem. 2003, 115, 1616; Angew. Chem. Int. Ed. 2003, 42, 1578;
5. b) L. Weber, Eur. J. Inorg. Chem. 2000, 2425;
6. c) M. Yoshifuji, J. Chem. Soc. Dalton Trans. 1998, 3343;
7. d) F. Mathey, Acc. Chem. Res. 1992, 25, 90;
8. e) R. Appel in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990, p. 157;
9. f) R. Appel, F. Knoll, Adv. Inorg. Chem. 1989, 33, 259;
10. g) J. F. Nixon, Chem. Rev. 1988, 88, 1327;
11. h) R. Appel, F. Knoll, I. Ruppert, Angew. Chem. 1981, 93, 771; Angew. Chem. Int. Ed. Engl. 1981, 20, 731.
12. h) R. Appel, F. Knoll, I. Ruppert, Angew. Chem. 1981, 93, 771; Angew. Chem. Int. Ed. Engl. 1981, 20, 731.
13. For a review highlighting some potential applications of compounds containing P=C bonds in catalysis, see: L. Weber, Angew. Chem. 2002, 114, 583; Angew. Chem. Int. Ed. 2002, 41, 563, and references therein.
14. For a review highlighting some potential applications of compounds containing P=C bonds in catalysis, see: L. Weber, Angew. Chem. 2002, 114, 583; Angew. Chem. Int. Ed. 2002, 41, 563, and references therein.
15. a) T. C. Klebach, R. Lourens, F. Bickelhaupt, J. Am. Chem. Soc. 1978, 100, 4886;
16. b) T. A. van der Knaap, T. C. Klebach, F. Visser, F. Bickelhaupt, P. Ros, E. J. Baerends, C. H. Stam, M. Konijn, Tetrahedron 1984, 40, 765;
17. c) O. Mundt, G. Becker, W. Uhl, Z. Anorg. Allg. Chem. 1986, 540/541, 319.
18. C.-W. Tsang, M. Yam, D. P. Gates, J. Am. Chem. Soc. 2003, 125, 1480.
19. For reviews, see: a) J. E. Mark, H. R. Allcock, R. West, Inorganic Polymers, Prentice-Hall, Englewood Cliffs, 1992;
20. b) H. R. Allcock, Chemistry and Applications of Polyphosphazenes, Wiley, New Jersey, 2003;
21. c) I. Manners, Angew. Chem. 1996, 108, 1712; Angew. Chem. Int. Ed. Engl. 1996, 35, 1602;
22. c) I. Manners, Angew. Chem. 1996, 108, 1712; Angew. Chem. Int. Ed. Engl. 1996, 35, 1602;
23. d) R. H. Neilson, P. Wisian-Neilson, Chem. Rev. 1988, 88, 541;
24. e) A. R. McWilliams, H. Dorn, I. Manners, Top. Curr. Chem. 2002, 220, 141;
25. e) J.-P. Majoral, A. M. Caminade, V. Maraval, Chem. Commun. 2002, 2929.
26. For recent work on main-chain-phosphorus polymers, see: a) R. C. Smith, J. D. Protasiewicz, J. Am. Chem. Soc. 2004, 126, 2268;
27. b) H. Dorn, J. M. Rodenzo, B. Brunnhöfer, E. Rivard, J. A. Massey, I. Manners, Macromolecules 2003, 36, 291;
28. c) Y. Morisaki, Y. Aiki, Y. Chujo, Macromolecules 2003, 36, 2594;
29. d) V. A. Wright, D. P. Gates, Angew. Chem. 2002, 114, 2495; ) Angew. Chem. Int. Ed. 2002, 41, 2389;
30. d) V. A. Wright, D. P. Gates, Angew. Chem. 2002, 114, 2495; ) Angew. Chem. Int. Ed. 2002, 41, 2389;
31. e) H. R. Allcock, S. D. Reeves, C. R. de Denus, C. A. Crane, Macromolecules 2001, 34, 748;
32. f) C. H. Walker, J. V. St. John, P. Wisian-Neilson, J. Am. Chem. Soc. 2001, 123, 3846;
33. g) C. Hay, C. Fischmeister, M. Hissler, L. Toupet, R. Réau, Angew. Chem. 2000, 112, 1882; Angew. Chem. Int. Ed. 2000, 39, 1812;
34. g) C. Hay, C. Fischmeister, M. Hissler, L. Toupet, R. Réau, Angew. Chem. 2000, 112, 1882; Angew. Chem. Int. Ed. 2000, 39, 1812;
35. h) B. L. Lucht, N. O. St. Onge, Chem. Commun. 2000, 2097;
36. i) T. J. Peckham, J. A. Massey, C. H. Honeyman, I. Manners, Macromolecules 1999, 32, 2830;
37. j) S. S. H. Mao, T. D. Tilley, Macromolecules 1997, 30, 5566.
38. 1H NMR spectroscopy does not give an accurate measure of the phosphaalkene content. For example, a polymer consisting entirely of the methylenephosphine unit would show a (aryl H):(alkyl H) ratio of 1.33 (i.e. 12 H/9 H), whereas the ratio for polystyrene would be 1.66 (5 H/ 3 H).
39. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
40. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
41. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
42. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
43. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
44. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
45. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
46. See, for example: C. U. Pittman, Jr. in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 553; D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345; T. J. Dickerson, N. N. Reed, K. D. Janda, Chem. Rev. 2002, 102, 3325; C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275; N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217; P. H. Toy, K. D. Janda, Acc. Chem. Res. 2000, 33, 546; S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217; S. J. Shuttleworth, S. M. Allin, R. D. Wilson, D. Nasturica, Synthesis 2000, 1035.
47. For leading references on Suzuki coupling in the presence of molecular phosphines, see, for example: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
48. b) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int. Ed. 2002, 41, 4176;
49. b) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int. Ed. 2002, 41, 4176;
50. c) M. Miura, Angew. Chem. 2004, 116, 2251; Angew. Chem. Int. Ed. 2004, 43, 2201;
51. c) M. Miura, Angew. Chem. 2004, 116, 2251; Angew. Chem. Int. Ed. 2004, 43, 2201;
52. d) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907; Angew. Chem. Int. Ed. 2004, 43, 1871;
53. d) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907; Angew. Chem. Int. Ed. 2004, 43, 1871;
54. e) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020.
55. For Suzuki coupling in the presence of insoluble phosphine polymers/resins, see: a) Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Org. Lett. 2002, 4, 3371;
56. b) T. J. Colacot, E. S. Gore, A. Kuber, Organometallics 2002, 21, 3301;
57. c) C. A. Parrish, S. L. Buchwald, J. Org. Chem. 2001, 66, 3820;
58. d) K. Inada, N. Miyaura, Tetrahedron 2000, 56, 8661;
59. e) Y. Uozumi, H. Danjo, T. Hayashi, J. Org. Chem. 1999, 64, 3384;
60. f) I. Fenger, C. Le Drian, Tetrahedron Lett. 1998, 39, 4287;
61. g) S.-B. Jang, Tetrahedron Lett. 1997, 38, 1793.
62. For soluble polymer-supported phosphines for Suzuki coupling, see: a) Q.-S. Hu, Y. Lu, Z.-Y. Tang, H.-B. Yu, J. Am. Chem. Soc. 2003, 125, 2856;
63. b) A. Datta, K. Ebert, H. Plenio, Organometallics 2003, 22, 4685.
64. Although not used in Suzuki reactions, a soluble poly(arylenediphosphine) has been used in other Pd-catalyzed reactions: c) T. Kanbara, S. Takase, R. Hayashi, S. Kagaya, K. Hasegawa, T. Yamamoto, J. Polym. Sci. Part A 2002, 40, 2637.
65. There are two possible explanations for the low catalytic activity observed with 2. One possibility is that steric bulk around the phosphorus center in 2 hinders coordination to Pd. A second possibility is that the high phosphorus density in 2 leads to multidentate coordination to Pd, thus rendering it inaccessible to substrates and inactive.
66. 2): M. Yam, C.-W. Tsang, K. Noonan, J. Kingsley, B. O. Patrick, D. P. Gates, unpublished results.