In situ generation of carbenes: A general and versatile platform for organocatalytic living polymerization

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 3046-3056

  Nyce, Gregory W ^a   Glauser, Thierry ^a   Connor, Eric F ^a   Möck, Andreas ^a   Waymouth, Robert M ^b   Hedrick, James L ^a  

^a IBM ALMADEN RESEARCH CENTER   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CATALYSIS; MOLECULAR STRUCTURE; PHASE TRANSITIONS; POLYMERIZATION; SUBSTITUTION REACTIONS;

CARBENES;

ORGANOMETALLICS;

CARBENOID; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; LACTONE; MONOMER; THIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; MISCIBILITY; MOLECULAR STABILITY; PHASE TRANSITION; POLYMERIZATION; RING OPENING METATHESIS POLYMERIZATION; STEREOSPECIFICITY;

EID: 0037433492     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021084+     Document Type: Article

References (125)

1. Borman, S. Chem. Eng. News 2002, 80, 33.
2. For example, see: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
3. (b) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
4. (c) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. J. Am. Chem. Soc. 2002, 124, 1842.
5. (d) Wang, L.; Luis, L. A.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
6. (e) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244.
7. (f) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874-9875.
8. (g) Paras, N. A.; MacMillan D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371.
9. (h) Fu, G. C. Acc. Chem. Res. 2000, 33, 412-420.
10. (i) Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234.
11. (j) Dong, V. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 113, 240.
12. (k) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
13. (l) Nederberg, F.; Connor, E. F.; Glauser, T.; Hedrick, J. L. Chem. Commun. 2001, 2066.
14. (m) List, B.; Lerner, R. A.; Barbas, C. A. J. Am. Chem. Soc. 2000, 122, 2395.
15. (n) Myers, M.; Connor, E.; Nyce, G.; Glauser, T.; Mock, A.; Hedrick, J. L. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 844.
16. (o) Nederberg, F.; Connor, E. F.; Moller, M.; Glauser, T.; Hedrick, J. L. Angew. Chem., Int. Ed. 2001, 40, 2712.
17. Connor, E. F.; Nyce, G. W.; Mock, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914.
18. (a) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587.
19. (b) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
20. (a) Albertsson, A.-C. Degradable Aliphatic Polyesters. Adv. Polym. Sci. 2002, 157.
21. (b) Trollsås, M.; Hedrick, J. L. J. Am. Chem. Soc. 1998, 120, 4644.
22. (c) Trollsås, M.; Claesson, H.; Atthoff, B.; Hedrick, J. L. Angew. Chem., Int. Ed. 1998, 37, 3132.
23. For example, see: (a) Löfgren, A.; Albertsson, A. C.; Dubois, P.; Jérôme, R. Recent Advances in Ring Opening Polymerization of Lactones and Related Compounds. J. Mater. Sci., Rev. Macromol. Chem. Phys. 1995, 35, 379.
24. (b) Kricheldorf, H. R.; Kreiser-Saunders, I. Makromol. Chem. 1990, 191, 1057.
25. (c) Kricheldorf, H. R.; Kreiser-Saunders, I.; Scharnagl, N. Makromol. Chem., Makromol. Symp. 1990, 32, 285.
26. (d) Dubois, P.; Jacobs, C.; Jérôme, R.; Teyssié, P. Macromolecules 1991, 24, 2266.
27. (e) Aubrecht, K. B.; Chang, M. A.; Hillmyer, M. A.; Tolman, W. B. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 284.
28. (f) Ovitt, T. M.; Coates, G. M. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4686.
29. (g) Kowalski, A.; Duda, A.; Penczek, S. Macromolecules 2000, 33, 689.
30. (h) Stevels, W. M.; Ankone, M. J. K.; Dijkstra, P. J.; Feijen, J. Macromolecules 1996, 29, 3441.
31. (a) Arduengo, A. J.; Dais, R. L.; Harlow, R.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
32. (b) Arduengo, A. J.; Dais, R. L.; Harlow, R.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
33. (a) Arduengo, A. J. Acc. Chem. Res. 1999, 32, 913.
34. (b) Arduengo, A. J.; Krfczyk, R. Chem. Z. 1998, 32, 6.
35. (c) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
36. (d) Herrmann, W.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
37. (e) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
38. (f) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
39. (g) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490.
40. (h) Herrmann, W. A.; Elison, M.; Fisher, J.; Kocher, C.; Artus, G. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371.
41. (i) Herrmann, W. A.; Goossen, L.; Kocher, C.; Artus, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805.
42. (j) Lappert, M. J. Organomet. Chem. 1988, 358, 185.
43. (k) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Henrique, T.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
44. For example, see: (a) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749.
45. (b) Herrman, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162.
46. (c) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648.
47. (d) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1998, 18, 2370.
48. For example, see: (a) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153.
49. (b) Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67.
50. (c) Jaarpour, L.; Nolan, S. P. Organometallics 2000, 19, 2055.
51. (d) Grasa, G. A.; Nolan, S. P. Organometallics 2001, 20, 3607.
52. (a) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217.
53. (b) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899.
54. (c) Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
55. (d) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
56. (a) Patten, T.; Matysjaszewski, K. J. Am. Chem. Soc. 1997, 23, 65.
57. (b) Coessens, V.; Pintauer, T.; Matyjaszewski, K. Prog. Polym. Sci. 2001, 26, 337.
58. (c) Tokuchi, K.; Ando, T.; Kamigaito, M.; Sawamoto, M. J. Polym. Sci., Polym. Chem. Ed. 2000, 38, 4735.
59. (d) Matyjaszewski, K. Controlled Radical Polymerization; Matyjaszewski, K., Ed.; ACS Symposium Series 685; American Chemical Society: Washigton, DC, 1998.
60. (e) Huan, K.; Bes, L.; Haddleton, D. M.; Khoshdel, E. J. Polym. Sci., Polym. Chem. Ed. 2001, 39, 1833.
61. (f) Asandei, A. D.; Percec, V. J. Polym. Sci., Polym. Chem. Ed. 2001, 39, 3392.
62. (g) Matyjaszewski, K.; Shipp, D. A.; McMurtry, G. P.; Gaynor, S. G.; Pakula, T. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 2023.
63. (h) Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661.
64. (i) Benoit, D.; Chaplinski, V.; Braslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904.
65. (j) Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185.
66. (k) Pasquale, A. J.; Long, T. E. J. Polym. Sci., Polym. Chem. Ed. 2001, 39, 216.
67. (l) Mayadunne, R. T. A.; Rizzardo, E.; Chiefari, J.; Krstina, J.; Moad, G.; Postma, A.; Thang, S. H. Macromolecules 2000, 33, 243.
68. Arduengo, A. J.; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523.
69. Kuhn, N.; Kratz, T. Synthesis 1993, 561.
70. Fuller, J.; Carlin, R. T.; Osteryoung, R. A. J. Electrochem. Soc. 1997, 144, 3881.
71. Stetter, H.; Kuhlmann Angew. Chem. 1974, 86, 589.
72. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
73. Although thiazole carbenes have a tendency to dimerize, Arduengo has recently reported a stable, sterically hindered carbene (3-(2,6-diisopropylphenyl)thiazole-2-ylidene). Arduengo, A. J.; Goerlich, J. R.; Marshall, W. J. Liebigs Ann./Recl. 1997, 365.
74. For example, see: Motesharei, K.; Myles, D. C. J. Am. Chem. Soc. 1997, 119, 6674.
75. Polymer supported catalysts were synthesized by reacting Merrifield resin with thiazole in 2-propanol at 60 °C for 3 days.
76. It was determined by control experiments that triethylamine does not catalyze the polymerization of lactide.
77. These conditions are consistent with a recent report of thiazolium catalyzed synthesis of α-amido ketones. For example, see: Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696.
78. (a) Arduengo, A. J. Acc. Chem. Res. 1999, 32, 913.
79. (b) Arduengo, A. J.; Krfczyk, R. Chem. Z. 1998, 32, 6.
80. (c) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
81. (d) Herrmann, W.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
82. (e) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
83. (f) Huang, J.; Stevens, E. D.; Nolan, S. P. Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
84. (g) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490.
85. (h) Herrmann, W. A.; Elison, M.; Fisher, J.; Kocher, C.; Artus, G. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371.
86. (i) Herrmann, W. A.; Goossen, L.; Kocher, C.; Artus, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805.
87. (j) Lappert, M. J. Organomet. Chem. 1988, 358, 185.
88. (k) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Henrique, T.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
89. 1H NMR spectra of the in situ catalysts were identical to values reported in the literature. Although tert-butyl alcohol is a byproduct of these reactions, we have seen no evidence of initiation of polymerization by tert-butyl alcohol.
90. Arduengo, A. J.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Khasnis, D.; Marshall, W. J.; Prakasha, T. K. J. Am. Chem. Soc. 1997, 119, 12742.
91. See ref 20 for reaction conditions.
92. Arduengo, A. J., III; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027.
93. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
94. (a) Wanzlick, H.-W.; Kleiner, H.-J. Angew. Chem. 1961, 73, 493.
95. (b) Wanzlick, H.-W. Angew. Chem. 1962, 74, 128.
96. (c) Wanzlick, H.-W.; Kleiner, H.-J. Chem. Ber. 1963, 96, 3024.
97. Van Hummel, G. J.; Harkema, S.; Kohn, F. E.; Feijen, Acta Crystallogr., Sect. B 1982, 38, 1679.
98. Gross, R. A.; Kumar, A.; Kalra, B. Chem. Rev. 2001, 101, 2097.
99. (a) Lyman, D. J.; Rowland, S. M. Biomaterials. Encyclopedia of Polymer Sciences and Engineering, 2nd ed.; 1985; Vol. 2, p 267.
100. (b) Schindler, A.; Jeffcoat, R.; Kimmel, G. L.; Pitt, C. G.; Wall, M. E.; Zweidinger, R. In Contemporary Topics in Polymer Science; Pearce, E. M., Schaefgen, J. R., Eds.; Plenum Press: New York, 1977; Vol. 2, p 251.
101. (c) Pett, C. G.; Marks, T. A.; Schindler, A. Biodegradeable Drug Delivery Systems based on aliphatic Polyesters: Application to Contraceptives and Narcotic Antagonists. In Controlled Release of Bioactive Materials; Baker, R., Ed.; Academic Press: New York, 1980.
102. Song, C. X.; Sun, H. F.; Feng, X. D. Polym. J. 1987, 19 (5), 485.
103. (a) Jacobs, C.; Dubois, Ph.; Jerome, R.; Teyssie, Ph. Macromolecules 1991, 24, 3027.
104. (b) Vanhoorne, P.; Dubois, Ph.; Jerome, R.; Teyssie, Ph. Macromolecules 1992, 25, 37.
105. Kricheldorf, H. R.; Jonte, J. M.; Berl, M. Makromol. Chem., Suppl. 1985, 12, 25.
106. Song, C. X.; Feng, X. D. Macromolecules 1984, 17, 2764.
107. For example, see: (a) Welton, T. Chem. Rev. 1999, 100, 2071.
108. (b) Olivier-Bourbigou, H. In Aqueous-Phase Organometallic Catalysis: Concepts and Applications; Cornils, B., Herrmann, W. A., Eds.: Wiley-VCH: Weinheim, Germany, 1998.
109. (c) Wilkes, J. S.; Levisky, J. A.; Wilson, R. A.; Hussy, C. L. Inorg. Chem. 1982, 21, 1263.
110. For example, see: (a) Carmichael, A. J.; Haddleton, D. M.; Bon, S. A.; Seddon, K. Chem. Commun. 2000, 1237.
111. (b) Carlin, R. T.; Wilkes, J. S. J. Mol. Catal. 1990, 63, 125.
112. For a few examples, see: (a) Chauvin, Y.; Mussman, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698.
113. (b) Tucker, C. E.; Jaeger, D. A. Tetrahedron Lett. 1989, 30, 1785.
114. (c) Kaufmann, D. E.; Nouroozian, M.; Henze, H. Synlett 1996, 1091.
115. (d) Carlin, R. T.; Wilkes, J. S. J. Mol. Catal. 1990, 63, 125.
116. (e) Chauvin, Y.; Einloft, S.; Olivier, H. Ind. Eng. Chem. Res. 1995, 34, 1149.
117. (f) Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; de Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217.
118. (g) Carmichael, A. J.; Haddleton, D. M.; Bon, S. A. F.; Seddon, K. R. Chem. Commun. 2000, 1237.
119. (a) Boon, J. A.; Levisky, J. A.; Pflug, J. L.; Wilkes, J. S. J. Org. Chem. 1986, 51, 480.
120. (b) Adams, C. J.; Earle, C. J.; Roberts, G.; Seddon, K. R. Chem. Commun. 1998, 2097.
121. (c) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. J. Am. Chem. Soc., published on the web.
122. (d) Green, L.; Hermeon, I.; Singer, R. D. Tetrahedron Lett. 2000, 41, 1343.
123. (e) Howarth, J.; Hanlon, K.; Fayne, D.; McCormac, P. Tetrahedron Lett. 1997, 38, 3097.
124. Davis, J. H., Jr.; Forrester, K. J. Tetrahedron Lett. 1999, 40, 1621.
125. Fuller, J.; Carlin, R. T.; Osteryoung, R. A. J. Electrochem. Soc. 1997, 144, 3881.