N-Heterocyclic carbenes: Effective organic catalysts for living polymerization

Polymer

Volumn 47, Issue 11, 2006, Pages 4018-4025

  Dove, Andrew P ^a   Pratt, Russell C ^a   Lohmeijer, Bas G G ^a   Culkin, Darcy A ^b   Hagberg, Eric C ^a   Nyce, Gregory W ^a   Waymouth, Robert M ^b   Hedrick, James L ^a  

^a IBM ALMADEN RESEARCH CENTER   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

Carbene; Lactide; Ring opening polymerization

Indexed keywords

CATALYST ACTIVITY; CATALYSTS; MONOMERS; RING OPENING POLYMERIZATION; SUBSTRATES;

CARBENE; CATALYST STABILITY; LACTIDE;

AROMATIC COMPOUNDS;

CATALYST; CONDENSATION; CONTROL; MOLECULAR WEIGHT; MONOMER; POLYMERIZATION; SUBSTRATE;

EID: 33646814779     PISSN: 00323861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymer.2006.02.037     Document Type: Article

References (126)

1. Dalko P.I., and Moisan L. Angew Chem Int 40 (2001) 3726
2. Cordova A., Notz W., Zhong G., Betancort J.M., and Barbas C.F. J Am Chem Soc 124 (2002) 1842
3. Cordova A., Notz W., Zhong G., Betancort J.M., and Barbas C.F. J Am Chem Soc 124 (2002) 1866
4. Juhl K., and Jorgensen K.A. Angew Chem, Int Ed 42 (2003) 1498
5. Halland N, Hansen T, Jorgensen KA. Angew Chem, Int Ed. Published on the web.
6. For example: (a). Ahrendt K.A., Borths C.J., and MacMillan D.W.C. J Am Chem Soc 122 (2000) 4243-4244
7. Jen W.S., Wiener J.J.M., and MacMillan D.W.C. J Am Chem Soc 122 (2000) 9874-9875
8. Miller S.J., Copeland G.T., Papaioanou N., Horstmann T.W., and Ruel E.M. J Am Chem Soc 120 (1998) 1629
9. For example: Guerin DJ, Miller SJ. J Am Chem Soc 2002;124:2134-2136.
10. For example: (a). Fu G.C. Acc Chem Res 33 (2000) 412-420
11. Arai S., Bellemin-Laponnaz S., and Fu G.C. Angew Chem, Int Ed 40 (2001) 234
12. Tao B., Lo M.C., and Fu G.C. J Am Chem Soc 123 (2001) 353-354
13. Fu G.C. Adv Organomet Chem 47 (2001) 101
14. Fu G.C. Pure Appl Chem 73 (2001) 347
15. Kawabata T., Nagato M., Takasu K., and Fuji K. J Am Chem Soc 119 (1997) 3169
16. Spivey A.C., Maddaford A., Leese D.P., and Redgrave A.J. J Chem Soc, Perkin Trans 1 (2001) 1785
17. Sano T., Imai K., Ohshi K., and Oriyama T. Tetrahedron Lett 39 (1998) 3529
18. Vedejs E., and Chen X. J Am Chem Soc 118 (1996) 1809
19. For example: (a). Taylor S.J., and Morken J.P. Science 280 (1998) 267
20. Su D.-W., Wang Y.-C., and Yan T.-H. Tetrahedron Lett 40 (1999) 4197-4198
21. Basel Y., and Hassner A. J Org Chem 65 (2000) 6368-6380
22. Decicco C.P., and Buckle R.N. J Org Chem 57 (1992) 1005-1008
23. Witzeman J.S., and Nottingham W.D. J Org Chem 56 (1991) 1713-1718
24. Hatakeyama S., Satoh K., Sakurai K., and Takano S. Tetrahedron Lett (1987) 2713-2716
25. For example: (a). List B. Adv Synth Catal 346 (2004) 1021
26. Borman S, C&E News 2002, February 25, p. 33.
27. For example: (a). Kumar A., and Gross R.A. J Am Chem Soc 122 (2000) 11767-11770
28. Kumar A., and Gross R.A. Biomacromolecules 1 (2000) 133-138
29. Kobayashi S., Uyama H., Namekawa S., and Hayakawa H. Macromolecules 31 (1998) 5655
30. Lei L, Breslow R, J Am Chem Soc 2002;124:4978-4979.
31. Nederberg F., Connor E.F., Moller M., Glauser T., and Hedrick J.L. Angew Chem, Int Eng Ed 40 (2001) 2712
32. Nederberg F., Connor E.F., Glauser T., and Hedrick J.L. Chem Commun (2001) 2066
33. Myers M., Connor E., Nyce G., Glauser T., Möck A., and Hedrick J.L. J Polym Sci, Part A: Polym Chem Ed 40 (2002) 844
34. This strategy was used by Wanzlick and coworkers to prepare 1,3-Bis(phenyl)-2-(trichlormethyl)imidazolidine see: (a). Wanzlick H.W., and Kleiner H.J. Angew Chem 73 (1961) 493
35. Wanzlick H.W. Angew Chem 1 (1962) 75
36. Wanzlick H.W., Esser T., and Kleiner H.J. Chem Ber 96 (1963) 1208
37. Denk M.K., Thadani A., Hatano K., and Lough A.J. Angew Chem 109 (1997) 2719
38. Denk M.K., Thadani A., Hatano K., and Lough A.J. Angew Chem, Int Ed Engl 36 (1997) 2607
39. Arduengo A.J., Dais R.L., Harlow R., and Kline M. J Am Chem Soc 113 (1991) 361
40. Arduengo A.J., Dais R.L., Harlow R., and Kline M. J Am Chem Soc 114 (1992) 5530
41. For example: (a). Igau A., Baceiredo A., Trinquier G., and Bertrand G. Angew Chem 101 (1989) 617
42. Igau A., Baceiredo A., Gruetzmacher H., and Bertrand G. J Am Chem Soc 110 (1988) 6463
43. Arduengo A.J. Acc Chem Res 32 (1999) 913
44. Arduengo A.J., and Krfczyk R. Chem Z 32 (1998) 6
45. Enders D., Breuer K., Raabe G., Runsink J., Henrique T., Melder J.-P., et al. Angew Chem, Int Ed Engl 34 (1995) 1021
46. Enders D., and Breuer J.H. Helv Chim Acta 79 (1996) 1217
47. Teles J., Melder J., Ebel K., Enders D., and Breuer J.H. Helv Chim Acta 79 (1996) 61
48. For example: (a). Bourissou D., Guerret O., Gabbai F.P., and Bertrand G. Chem Rev 100 (2000) 39
49. Herrmann W., and Köcher C. Angew Chem, Int Ed Engl 36 (1997) 2162
50. Scholl M., Trnka T.M., Morgan J.P., and Grubbs R.H. Tetrahedron Lett 40 (1999) 2247
51. Huang J., Stevens E.D., Nolan S.P., and Petersen J.L. J Am Chem Soc 121 (1999) 2674
52. Weskamp T., Schattenmann W.C., Spiegler M., and Herrmann W.A. Angew Chem 110 (1998) 2631
53. Weskamp T., Schattenmann W.C., Spiegler M., and Herrmann W.A. Angew Chem, Int Ed Engl 37 (1998) 2490
54. Herrmann W.A., Elison M., Fisher J., Köcher C., and Artus G.J. Angew Chem 107 (1995) 2602
55. Herrmann W.A., Elison M., Fisher J., Köcher C., and Artus G.J. Angew Chem, Int Ed Engl 34 (1995) 2371
56. Herrmann W.A., Goossen L., Köcher C., and Artus G.J. Angew Chem 108 (1996) 2980
57. Herrmann W.A., Goossen L., Köcher C., and Artus G.J. Angew Chem, Int Ed Engl 35 (1996) 2805
58. Lappert M.J. J Organomet Chem 358 (1988) 185
59. Enders D., Breuer K., Raabe G., Runsink J., Henrique T., Melder J.-P., et al. Angew Chem 107 (1995) 2602
60. Enders D., Breuer K., Raabe G., Runsink J., Henrique T., Melder J.-P., et al. Angew Chem, Int Ed Engl 34 (1995) 1021
61. For example: (a). Herrmann W.A. Angew Chem 114 (2002) 1342
62. Herrmann W.A. Angew Chem, Int Ed Engl 41 (2002) 1290
63. Sanford M.S., Ulman M., and Grubbs R.H. J Am Chem Soc 123 (2001) 749
64. Herrmann W.A., Goossen L.J., and Spiegler M. Organometallics 17 (1998) 2162
65. Choi T.-L., and Grubbs R.H. Chem Commun (2001) 2648
66. Haung J., Schanz H.-J., Stevens E.D., and Nolan S.P. Organometallics 18 (1998) 2370
67. Breslow R. J Am Chem Soc 80 (1958) 3719
68. Stetter H. Angew Chem 88 (1976) 695
69. Stetter H. Angew Chem, Int Ed Engl 15 (1976) 639
70. Enders D., and Breuer J.H. Helv Chim Acta 79 (1996) 1217
71. Teles J., Melder J., Ebel K., Enders D., and Breuer J.H. Helv Chim Acta 79 (1996) 61
72. Kerr M.S., Read De Alaniz J., and Rovis T. J Am Chem Soc 124 (2002) 10298
73. Enders D., and Kallfass U. Angew Chem 114 (2002) 1822
74. Enders D., and Kallfass U. Angew Chem, Int Ed Engl 41 (2002) 1743
75. Connor E.F., Nyce G.W., Myers M., Möck A., and Hedrick J.L. J Am Chem Soc 12 (2002) 914
76. Nyce G.W., Glauser T., Connor E.F., Möck A., Waymouth R.M., and Hedrick J.L. J Am Chem Soc 125 (2003) 3046
77. Grassa G.A., Guveli T., Singh R., and Nolan S.P. J Org Chem 68 (2003) 2812
78. Hedrick J.L., Magbitang T., Connor E.F., Glauser T., Volksen W., Hawker C.J., et al. Chem-Eur J 8 (2002) 3308
79. Hachisu Y., Bode J.W., and Suzuki K. Adv Synth Catal 346 (2004) 1097
80. Chsihony S., Beaudette T.T., Sentman A.C., Nyce G.W., Waymouth R.W., and Hedrick J.L. Adv Synth Catal 346 (2004) 1081
81. For example: (a). Kerr M.S., Read de Alaniz J., and Rovis T. J Am Chem Soc 123 (2002) 10298
82. Enders D., and Kallfass U. Angew Chem, Int Ed Engl 41 (2002) 1743
83. Breslow R.J. Am. Chem. Soc. 80 (1958) 3719
84. Kerr M.S., De Alaniz J.R., and Rovis T. J Am Chem Soc 124 (2002) 10298
85. Murry J.A., Frantz D.E., Soheili A., Tillyer R., Grabowski E.J.J., and Reider P.J. J Am Chem Soc 123 (2001) 9696
86. Grasa G.A., Kissling R.M., and Nolan S.P. Org Lett 4 (2002) 3583-3586
87. Nyce G.W., Lamboy J.A., Connor E.F., Waymouth R.M., and Hedrick J.L. Org Lett 4 (2002) 3587-3590
88. Sohn S.S., Rosen E.L., and Bode W.J. J Am Chem Soc 126 44 (2004) 14370
89. Patten T., and Matysjaszewski K. J Am Chem Soc 23 (1997) 65
90. Coessens V., Pintauer T., and Matyjaszewski K. Prog Polym Sci 26 (2001) 337
91. Tokuchi K., Ando T., Kamigaito M., and Sawamoto M. J Polym Sci, Polym Chem Ed 38 (2000) 4735
92. Matyjaszewski K. In: Matyjaszewski K. (Ed). Controlled radical polymerization. ACS Symp Ser 685 (1998), American Chemical Society, Washigton, DC
93. Huan K., Bes L., Haddleton D.M., and Khoshdel E. J Polym Sci, Polym Chem Ed 39 (2001) 1833
94. Asandei A.D., and Percec V. J Polym Sci, Polym Chem Ed 39 (2001) 3392
95. Matyjaszewski K., Shipp D.A., McMurtry G.P., Gaynor S.G., and Pakula T. J Polym Sci, Part A: Polym Chem Ed 38 (2000) 2023
96. Hawker C.J., Bosman A.W., and Harth E. Chem Rev 101 (2001) 3661
97. Benoit D., Chaplinski V., Braslau R., and Hawker C.J. J Am Chem Soc 121 (1999) 3904
98. Hawker C.J. J Am Chem Soc 116 (1994) 11185
99. Pasquale A.J., and Long T.E. J Polym Sci, Polym Chem Ed 39 (2001) 216
100. Mayadunne R.T.A., Rizzardo E., Chiefari J., Krstina J., Moad G., Postma A., et al. Macromolecules 33 (2000) 243
101. Lutz J.-F., Jahed N., and Matyjaszewski K. J Polym Sci, Polym Chem Ed 42 (2004) 1939
102. Ando T., Sawauchi C., Ouchi M., Kamigaito M., and Sawamoto M. J Polym Sci, Polym Chem Ed 41 (2003) 3597
103. Monge S., Darcos V., and Haddleton D.M. J Polym Sci, Polym Chem Ed 42 (2004) 6299
104. Arduengo A.J., Davidson F., Dias H.V.R., Goerlich J.R., Khasnis D., Marshall W.J., et al. J Am Chem Soc 119 (1997) 12742
105. Arduengo III A.J., Goerlich J.R., and Marshall W.J. J Am Chem Soc 117 (1995) 11027
106. Wanzlick H.-W., and Kleiner H.-J. Angew Chem 73 (1961) 493
107. Wanzlick H.-W. Angew Chem 74 (1962) 128
108. Wanzlick H.-W., and Kleiner H.-J. Chem Ber 96 (1963) 3024
109. For example: (a). Welton T. Chem Rev (1999) 2071-2083
110. Olivier-Bourbigou H. In: Cornils B., and Herrmann W.A. (Eds). Aqueous-phase organometallic catalysis: concepts and applications (1998), Wiley-VCH, Weinheim
111. Wilkes J.S., Levisky J.A., Wilson R.A., and Hussy C.L. Inorg Chem 21 (1982) 1263
112. Arduengo A.J., Calabrese J.C., Davidson F., Dias H.V.R., Goerlich J.R., Krafczyk R., et al. Helv Chim Acta 82 (1999) 2348
113. Wanzlick H.W., and Ahrens H. Chem Ber 99 (1966) 1580
114. Wanzlick H.W., and Kleiner H.J. Chem Ber 96 (1963) 3024
115. Enders D., Breuer K., Runsink J., and Teles J.H. Liebigs Ann Chem (1996) 2019
116. Cetinkaya B., Cetinkaya E., Chamizo J.A., Hitchcock P.B., Jasim H.A., Kücükbay H., et al. J Chem Soc, Perkin Trans 1 (1998) 2047-2054
117. Wanzlick H.-W., Esser F., and Kleiner H.-J. Chem Ber (1963) 1208-1212
118. Trnka T.M., Morgan J.P., Sanford M.S., Wilhelm T.E., Scholl M., Choi T.-L., et al. J Am Chem Soc 12 (2003) 2546
119. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org Lett 1 (1999) 953
120. Viciu M.S., Zinn F.K., Stevens E.D., and Nolan S.P. Organometallics 22 (2003) 3175
121. Enders D., Breuer K., Raabe G., Runsink J., Teles J.H., Melder J.P., et al. Angew Chem 107 (1995) 1119
122. Enders D., Breuer K., Raabe G., Runsink J., Teles J.H., Melder J.P., et al. Angew Chem, Int Ed Engl 34 (1995) 1021
123. Denk K., Sirsch P., and Herrmann W.A. J Organomet Chem 649 (2002) 219-224
124. Randl S., Gessler S., Wakamatsu H., and Blechert S. Synlett 3 (2001) 430-432
125. Nyce G.W., Csihony S., Waymouth R.M., and Hedrick J.L. Chem-Eur J 10 (2004) 4073-4079
126. Csihong S, Culkin DA, Sentman AD, Dove AP, Waymouth RM, Hendrick JL. J Am Chem Soc 2005;127:9079-9084.