Review
Discrete Metal-Based Catalysts for the Copolymerization of CO2 and Epoxides: Discovery, Reactivity, Optimization, and Mechanism
Geoffrey W. Coates Prof.,
David R. Moore Dr.,
Geoffrey W. Coates Prof.
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853-1301, USA, Fax: (+1) 607-255-4137
Search for more papers by this authorDavid R. Moore Dr.
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853-1301, USA, Fax: (+1) 607-255-4137
Search for more papers by this authorGeoffrey W. Coates Prof.,
David R. Moore Dr.,
Geoffrey W. Coates Prof.
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853-1301, USA, Fax: (+1) 607-255-4137
Search for more papers by this authorDavid R. Moore Dr.
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14853-1301, USA, Fax: (+1) 607-255-4137
Search for more papers by this authorGraphical Abstract
Given the non-renewable nature of synthetic polymers from petroleum feedstocks, there is increasing interest in developing routes to biodegradable polymeric materials from renewable resources. Polycarbonates made from CO2 and epoxides (see scheme) have the potential to meet these important goals. Reviewed here are well-defined catalysts for epoxide–CO2 copolymerization and related reactions.
Abstract
Most synthetic polymers are made from petroleum feedstocks. Given the non-renewable nature of these materials, there is increasing interest in developing routes to polymeric materials from renewable resources. In addition, there is a growing demand for biodegradable polymeric materials. Polycarbonates made from CO2 and epoxides have the potential to meet these goals. Since the discovery of catalysts for the copolymerization of CO2 and epoxides in the late 1960's by Inoue, a significant amount of research has been directed toward the development of catalysts of improved activity and selectivity. Reviewed here are well-defined catalysts for epoxide–CO2 copolymerization and related reactions.
References
- 1T. U. Gerngross, S. C. Slater, Sci. Am. 2000, 283( 2), 36–41.
- 2R. A. Gross, B. Kalra, Science 2002, 297, 803–807.
- 3M. Okada, Prog. Polym. Sci. 2002, 27, 87–133.
- 4H. Danner, R. Braun, Chem. Soc. Rev. 1999, 28, 395–405.
- 5H. Arakawa, M. Aresta, J. N. Armor, M. A. Barteau, E. J. Beckman, A. T. Bell, J. E. Bercaw, C. Creutz, E. Dinjus, D. A. Dixon, K. Domen, D. L. DuBois, J. Eckert, E. Fujita, D. H. Gibson, W. A. Goddard, D. W. Goodman, J. Keller, G. J. Kubas, H. H. Kung, J. E. Lyons, L. E. Manzer, T. J. Marks, K. Morokuma, K. M. Nicholas, R. Periana, L. Que, J. Rostrup-Nielson, W. M. H. Sachtler, L. D. Schmidt, A. Sen, G. A. Somorjai, P. C. Stair, B. R. Stults, W. Tumas, Chem. Rev. 2001, 101, 953–996.
- 6W. Leitner, C. R. Acad. Sci. Ser. IIc 2000, 3, 595–600.
- 7A. I. Cooper, J. Mater. Chem. 2000, 10, 207–234.
- 8C. Bolm, O. Beckmann, O. A. G. Dabard, Angew. Chem. 1999, 111, 957–959;
Angew. Chem. Int. Ed. 1999, 38, 907–909.
10.1002/(SICI)1521-3773(19990401)38:7<907::AID-ANIE907>3.0.CO;2-# CAS PubMed Web of Science® Google Scholar
- 9For leading references on CO2 fixation and/or catalysis, see:
- 9aG. Musie, M. Wei, B. Subramaniam, D. H. Busch, Coord. Chem. Rev. 2001, 219, 789–820;
- 9bW. Leitner, Coord. Chem. Rev. 1996, 153, 257–284;
- 9cW. Leitner, Angew. Chem. 1995, 107, 2391–2405; Angew. Chem. Int. Ed. Engl. 1995, 34, 2207–2221.
- 10M. Shi, Y. M. Shen, Curr. Org. Chem. 2003, 7, 737–745.
- 11X. Yin, J. R. Moss, Coord. Chem. Rev. 1999, 181, 27–59.
- 12D. Walther, M. Ruben, S. Rau, Coord. Chem. Rev. 1999, 182, 67–100.
- 13A. Behr, Carbon Dioxide Activation by Metal Complexes, VCH, Weinheim, 1988.
- 14D. H. Gibson, Chem. Rev. 1996, 96, 2063–2095.
- 15D. Walther, Coord. Chem. Rev. 1987, 79, 135–174.
- 16P. G. Jessop, T. Ikariya, R. Noyori, Chem. Rev. 1999, 99, 475–493.
- 17J. L. Kendall, D. A. Canelas, J. L. Young, J. M. DeSimone, Chem. Rev. 1999, 99, 543–563.
- 18S. Inoue, CHEMTECH 1976, 6, 588–594.
- 19W. Kuran, Prog. Polym. Sci. 1981, 23, 919–992.
- 20D. J. Darensbourg, M. W. Holtcamp, Coord. Chem. Rev. 1996, 153, 155–174.
- 21M. S. Super, E. J. Beckman, Trends Polym. Sci. 1997, 5, 236–240.
- 22E. J. Beckman, Science 1999, 283, 946–947.
- 23D. X. Wang, M. Q. Kang, X. K. Wang, Prog. Chem. 2002, 14, 462–468.
- 24H. Pang, B. Liao, Y. H. Huang, G. M. Cong, Chin. J. Appl. Chem. 2001, 18, 347–350.
- 25http://www.empowermaterials.com (accessed April 25, 2004).
- 26S. D. Thorat, P. J. Phillips, V. Semenov, A. Gakh, J. Appl. Polym. Sci. 2003, 89, 1163–1176.
- 27S. M. Peng, Y. An, C. Chen, B. Fei, Y. Zhuang, L. Dong, Polym. Degrad. Stab. 2003, 80, 141–147.
- 28B. Liu, L. Chen, M. Zhang, A. Yu, Macromol. Rapid Commun. 2002, 23, 881–884.
- 29S. J. Wang, L. C. Du, X. S. Zhao, Y. Z. Meng, S. C. Tjong, J. Appl. Polym. Sci. 2002, 85, 2327–2334.
- 30T. Sarbu, T. Styranec, E. J. Beckman, Nature 2000, 405, 165–168.
- 31C. Koning, J. Wildeson, R. Parton, B. Plum, P. Steeman, D. J. Darensbourg, Polymer 2001, 42, 3995–4004.
- 32C. K. Harnett, G. W. Coates, H. G. Craighead, J. Vac. Sci. Technol. B 2001, 19, 2842–2845.
- 33C. K. Harnett, K. M. Satyalakshmi, G. W. Coates, H. G. Craighead, J. Photopolym. Sci. Technol. 2002, 15, 493–496.
- 34D. A. Czaplewski, J. Kameoka, R. Mathers, G. W. Coates, H. G. Craighead, Appl. Phys. Lett. 2003, 83, 4836–4838.
- 35J. P. Jayachandran, H. A. Reed, H. Zhen, L. F. Rhodes, C. L. Henderson, S. A. B. Allen, P. A. Kohl, J. Microelectromech. Syst. 2003, 12, 147–159.
- 36A. G. Shaikh, Chem. Rev. 1996, 96, 951–976.
- 37J. H. Clements, Ind. Eng. Chem. Res. 2003, 42, 663–674.
- 38A. Rokicki, Prog. Polym. Sci. 2000, 25, 259–342.
- 39G. W. Coates, Chem. Rev. 2000, 100, 1223–1252.
- 40G. W. Coates, P. D. Hustad, S. Reinartz, Angew. Chem. 2002, 114, 2340–2361;
10.1002/1521-3757(20020703)114:13<2340::AID-ANGE2340>3.0.CO;2-Z Google ScholarAngew. Chem. Int. Ed. 2002, 41, 2236–2257.
- 41B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, J. Chem. Soc. Dalton Trans. 2001, 2215–2224.
- 42R. H. Grubbs, Handbook of Metathesis, Wiley, New York, 2003.
10.1002/9783527619481 Google Scholar
- 43G. W. Coates, J. Chem. Soc. Dalton Trans. 2002, 467–475.
- 44S. Inoue, H. Koinuma, T. Tsuruta, J. Polym. Sci. Part B 1969, 7, 287–292.
- 45S. Inoue, H. Koinuma, T. Tsuruta, Makromol. Chem. 1969, 130, 210–220.
- 46M. Kobayashi, S. Inoue, T. Tsuruta, Macromolecules 1971, 4, 658–659.
- 47M. Kobayashi, Y. L. Tang, T. Tsuruta, S. Inoue, Makromol. Chem. 1973, 169, 69–81.
- 48M. Kobayashi, S. Inoue, T. Tsuruta, J. Polym. Sci. Polym. Chem. Ed. 1973, 11, 2383–2385.
- 49S. Inoue, M. Kobayashi, H. Koinuma, T. Tsuruta, Makromol. Chem. 1972, 155, 61–73.
- 50W. Kuran, S. Pasynkiewicz, J. Skupinska, A. Rokicki, Makromol. Chem. Macromol. Chem. Phys. 1976, 177, 11–20.
- 51P. Gorecki, W. Kuran, J. Polym. Sci. Part C 1985, 23, 299–304.
- 52W. Kuran, T. Listos, Macromol. Chem. Phys. 1994, 195, 977–984.
- 53K. Soga, E. Imai, I. Hattori, Polym. J. 1981, 13, 407–410.
- 54Y. Hino, Polym. J. 1984, 16, 159–163.
- 55T. Tsuruta, Makromol. Chem. 1986, 6, 23–31.
- 56W. Kuran, Appl. Organomet. Chem. 1991, 5, 191–194.
- 57W. Kuran, T. Listos, Macromol. Chem. Phys. 1994, 195, 1011–1015.
- 58W. Kuran, T. Listos, Pol. J. Chem. 1994, 68, 1071–1083.
- 59S. Inoue, H. Koinuma, Y. Yokoo, T. Tsuruta, Makromol. Chem. 1971, 143.
- 60S. Inoue, J. Polym. Sci. Part A 2000, 38, 2861–2871.
- 61N. Takeda, S. Inoue, Makromol. Chem. 1978, 179, 1377–1381.
- 62T. Aida, S. Inoue, Macromolecules 1981, 14, 1162–1166.
- 63T. Aida, S. Inoue, Macromolecules 1981, 14, 1166–1169.
- 64T. Aida, S. Inoue, Macromolecules 1982, 15, 682–684.
- 65T. Aida, S. Inoue, J. Am. Chem. Soc. 1983, 105, 1304–1309.
- 66T. Aida, S. Inoue, J. Am. Chem. Soc. 1985, 107, 1358–1364.
- 67T. Aida, M. Ishikawa, S. Inoue, Macromolecules 1986, 19, 8–13.
- 68J. H. Jung, M. Ree, T. Chang, J. Polym. Sci. Part A 1999, 37, 3329–3336.
10.1002/(SICI)1099-0518(19990815)37:16<3329::AID-POLA31>3.0.CO;2-Q CAS Web of Science® Google Scholar
- 69K. Kasuga, S. Nagao, T. Fukumoto, M. Handa, Polyhedron 1996, 15, 69–72.
- 70K. Shimasaki, T. Aida, S. Inoue, Macromolecules 1987, 20, 3076–3080.
- 71Y. Watanabe, T. Yasuda, T. Aida, S. Inoue, Macromolecules 1992, 25, 1396–1400.
- 72H. Sugimoto, H. Ohshima, S. Inoue, J. Polym. Sci. Part A 2003, 41, 3549–3555.
- 73X. B. Lu, X. J. Feng, R. He, Appl. Catal. A 2002, 234, 25–33.
- 74X. B. Lu, R. He, C. X. Bai, J. Mol. Catal. A 2002, 186, 1–11.
- 75D. J. Darensbourg, E. L. Maynard, M. W. Holtcamp, K. K. Klausmeyer, J. H. Reibenspies, Inorg. Chem. 1996, 35, 2682–2684.
- 76W. Kuran, T. Listos, M. Abramczyk, A. Dawidek, J. Macromol. Sci. Pure Appl. Chem. 1998, 35, 427–437.
- 77T. Sarbu, E. J. Beckman, Macromolecules 1999, 32, 6904–6912.
- 78T. Sarbu, T. J. Styranec, E. J. Beckman, Ind. Eng. Chem. Res. 2000, 39, 4678–4683.
- 79W. J. Kruper, D. V. Dellar, J. Org. Chem. 1995, 60, 725–727.
- 80W. J. Kruper, D. Dellar, US Patent 4,663,467, 1987 [ Chem. Abstr. 1987, 107, 98598b].
- 81S. Mang, A. I. Cooper, M. E. Colclough, N. Chauhan, A. B. Holmes, Macromolecules 2000, 33, 303–308.
- 82A. B. Holmes, S. A. Mang (Secretary of State for Defence, UK; Qinetiq Ltd.), Brit. UK Pat. Appl. 2352449, 2001 [ Chem. Abstr. 2001, 134, 237964].
- 83L. M. Stamp, S. A. Mang, A. B. Holmes, K. A. Knights, Y. R. de Miguel, I. F. McConvey, Chem. Commun. 2001, 2502–2503.
- 84For asymmetric ring-opening of epoxides using Cr or Co salen complexes, see the following and references therein:
- 84aE. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421–431;
- 84bJ. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1374–1377;
10.1002/1521-3757(20020415)114:8<1432::AID-ANGE1432>3.0.CO;2-6 Google ScholarAngew. Chem. Int. Ed. 2002, 41, 1374–1377;10.1002/1521-3773(20020415)41:8<1374::AID-ANIE1374>3.0.CO;2-8 CAS PubMed Web of Science® Google Scholar
- 84cS. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307–1315;
- 84dJ. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687–2688;
- 84eR. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10 780–10 781;
- 84fK. B. Hansen, J. L. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10 924–10 925.
- 85E. N. Jacobsen, M. Tokunaga, J. F. Larrow, PCT Int. Appl. WO 00/09463, 2000.
- 86R. L. Paddock, S. T. Nguyen, J. Am. Chem. Soc. 2001, 123, 11 498–11 499.
- 87D. J. Darensbourg, J. C. Yarbrough, J. Am. Chem. Soc. 2002, 124, 6335–6342.
- 88D. J. Darensbourg, J. L. Rodgers, C. C. Fang, Inorg. Chem. 2003, 42, 4498–4500.
- 89D. J. Darensbourg, J. C. Yarbrough, C. Ortiz, C. C. Fang, J. Am. Chem. Soc. 2003, 125, 7586–7591.
- 90R. Eberhardt, M. Allmendinger, B. Rieger, Macromol. Rapid Commun. 2003, 24, 194–196.
- 91K. Soga, K. Uenishi, S. Ikeda, J. Polym. Sci. Polym. Sci. Ed. 1979, 17, 415–423.
- 92Y. M. Shen, W. L. Duan, M. Shi, J. Org. Chem. 2003, 68, 1559–1562.
- 93Z. Q. Qin, C. M. Thomas, S. Lee, G. W. Coates, Angew. Chem. 2003, 115, 5642–5645; Angew. Chem. Int. Ed. 2003, 42, 5484–5487.
- 94R. Paddock, Y. Hiyama, J. McKay, S. Nguyen, Tetrahedron Lett. 2004, 45, 2023–2026.
- 95X. B. Lu, B. Liang, Y. J. Zhang, Y. Z. Tian, Y. M. Wang, C. X. Bai, H. Wang, R. Zhang, J. Am. Chem. Soc. 2004, 126, 3732–3733.
- 96X. H. Chen, Z. Q. Shen, Y. F. Zhang, Macromolecules 1991, 24, 5305–5308.
- 97Z. Q. Shen, X. H. Chen, Y. F. Zhang, Macromol. Chem. Phys. 1994, 195, 2003–2011.
- 98J. T. Guo, X. Y. Wang, Y. S. Xu, J. W. Sun, J. Appl. Polym. Sci. 2003, 87, 2356–2359.
- 99C. S. Tan, T. J. Hsu, Macromolecules 1997, 30, 3147–3150.
- 100T. J. Hsu, C. S. Tan, Polymer 2001, 42, 5143–5150.
- 101Z. Quan, X. H. Wang, X. J. Zhao, F. S. Wang, Polymer 2003, 44, 5605–5610.
- 102B. Y. Liu, X. J. Zhao, X. H. Wang, F. S. Wang, J. Polym. Sci. Part A 2001, 39, 2751–2754.
- 103A. Rokicki (Air Products and Chemicals, Inc., and Arco Chemical Co.), US Pat. App., 1990, US 4,943,677 [ Chem. Abstr. 1990, 113, 192136].
- 104S. A. Motika, T. L. Pickering, A. Rokicki, B. K. Stein (Air Products and Chemicals, Inc., Arco Chemical Co., and Mitsui Petrochemical Industries Ltd.), US Pat. App., 1991, US Patent 5,026,676 [ Chem. Abstr. 1991, 115, 93209].
- 105H. N. Sun, (Arco Chemical Co.), US Pat. App., 1988, US Patent 4,783,445 [ Chem. Abstr. 1988, 110, 135920].
- 106H. Kawachi, S. Minami, J. Armor, A. Rokicki, B. Stein, US Pat. App., 1991, US Patent 4,981,948 [ Chem. Abstr. 1990, 113, 24673].
- 107M. Ree, J. Y. Bae, J. H. Jung, T. J. Shin, Korea Polym. J. 1999, 7, 333–349.
- 108M. Ree, J. Y. Bae, J. H. Jung, T. J. Shin, J. Polym. Sci. Part A 1999, 37, 1863–1876.
10.1002/(SICI)1099-0518(19990615)37:12<1863::AID-POLA16>3.0.CO;2-K CAS Web of Science® Google Scholar
- 109M. Ree, J. Y. Bae, J. H. Jung, T. J. Shin, Y. T. Hwang, T. Chang, Polym. Eng. Sci. 2000, 40, 1542–1552.
- 110D. J. Darensbourg, N. W. Stafford, T. Katsurao, J. Mol. Catal. A 1995, 104, L 1–L4.
- 111Y. Z. Meng, L. C. Du, S. C. Tiong, Q. Zhu, A. S. Hay, J. Polym. Sci. Part A 2002, 40, 3579–3591.
- 112Y. Q. Zheng, J. L. Lin, H. L. Zhang, Z. Kristallogr. New Cryst. Struct. 2000, 215, 535–536.
- 113R. Eberhardt, M. Allmendinger, M. Zintl, C. Troll, G. A. Luinstra, B. Rieger, Macromol. Chem. Phys. 2004, 205, 42–47.
- 114Y. T. Hwang, J. H. Jung, M. Ree, H. S. Kim, Macromolecules 2003, 36, 8210–8212.
- 115L. B. Chen, H. S. Chen, J. Lin, J. Macromol. Sci. Chem. 1987, 24, 253–260.
- 116T. Listos, W. Kuran, R. Siwiec, J. Macromol. Sci. Pure Appl. Chem. 1995, 32, 393–403.
- 117M. S. Super, E. Berluche, C. Costello, E. J. Beckman, Macromolecules 1997, 30, 368–372.
- 118D. J. Darensbourg, M. S. Zimmer, Macromolecules 1999, 32, 2137–2140.
- 119W. J. Kruper, D. J. Smart (The Dow Chemical Co.), US Patent 4,500,704, 1983.
- 120L. B. Chen, Makromol. Chem. Macromol. Symp. 1992, 59, 75–82.
- 121D. J. Darensbourg, M. J. Adams, J. C. Yarbrough, Inorg. Chem. 2001, 40, 6543–6544.
- 122D. J. Darensbourg, M. J. Adams, J. C. Yarbrough, A. L. Phelps, Inorg. Chem. 2003, 42, 7809–7818.
- 123D. J. Darensbourg, M. W. Holtcamp, Macromolecules 1995, 28, 7577–7579.
- 124D. J. Darensbourg, M. W. Holtcamp, G. E. Struck, M. S. Zimmer, S. A. Niezgoda, P. Rainey, J. B. Robertson, J. D. Draper, J. H. Reibenspies, J. Am. Chem. Soc. 1999, 121, 107–116.
- 125D. J. Darensbourg, J. R. Wildeson, J. C. Yarbrough, J. H. Reibenspies, J. Am. Chem. Soc. 2000, 122, 12 487–12 496.
- 126D. J. Darensbourg, J. R. Wildeson, S. J. Lewis, J. C. Yarbrough, J. Am. Chem. Soc. 2002, 124, 7075–7083.
- 127D. J. Darensbourg, M. S. Zimmer, P. Rainey, D. L. Larkins, Inorg. Chem. 2000, 39, 1578–1585.
- 128M. B. Dinger, M. J. Scott, Inorg. Chem. 2001, 40, 1029–1036.
- 129D. J. Darensbourg, M. W. Holtcamp, B. Khandelwal, K. K. Klausmeyer, J. H. Reibenspies, J. Am. Chem. Soc. 1995, 117, 538–539.
- 130D. J. Darensbourg, S. A. Niezgoda, M. W. Holtcamp, J. D. Draper, J. H. Reibenspies, Inorg. Chem. 1997, 36, 2426–2432.
- 131S. C. Goel, M. Y. Chiang, W. E. Buhro, J. Am. Chem. Soc. 1990, 112, 6724–6725.
- 132D. J. Darensbourg, S. A. Niezgoda, J. H. Reibenspies, J. D. Draper, Inorg. Chem. 1997, 36, 5686–5688.
- 133D. J. Darensbourg, S. A. Niezgoda, J. D. Draper, J. H. Reibenspies, J. Am. Chem. Soc. 1998, 120, 4690–4698.
- 134D. J. Darensbourg, J. R. Wildeson, J. C. Yarbrough, Inorg. Chem. 2002, 41, 973–980.
- 135D. J. Darensbourg, P. Rainey, J. C. Yarbrough, Inorg. Chem. 2001, 40, 986–993.
- 136D. J. Darensbourg, J. R. Wildeson, J. C. Yarbrough, Organometallics 2001, 20, 4413–4417.
- 137M. H. Chisholm, J. C. Gallucci, H. H. Zhen, J. C. Huffman, Inorg. Chem. 2001, 40, 5051–5054.
- 138O. Hampel, C. Rode, D. Walther, R. Beckert, H. Görls, Z. Naturforsch. B 2002, 57, 946–956.
- 139H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang, S. O. Kang, Angew. Chem. 2000, 112, 4262–4264;
Angew. Chem. Int. Ed. 2000, 39, 4096–4098.
10.1002/1521-3773(20001117)39:22<4096::AID-ANIE4096>3.0.CO;2-9 CAS PubMed Web of Science® Google Scholar
- 140H. S. Kim, J. J. Kim, S. D. Lee, M. S. Lah, D. Moon, H. G. Jang, Chem. Eur. J. 2003, 9, 678–686.
- 141D. J. Darensbourg, S. J. Lewis, J. L. Rodgers, J. C. Yarbrough, Inorg. Chem. 2003, 42, 581–589.
- 142I. Kim, S. M. Kim, C. S. Ha, D. W. Park, Macromol. Rapid Commun. 2004, 25, 888–893.
- 143M. Cheng, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 1998, 120, 11 018–11 019.
- 144G. W. Coates, M. Cheng, E. B. Lobkovsky, Abstr. Pap. Am. Chem. Soc. 1999, 217, 077-PMSE.
- 145M. Cheng, N. A. Darling, E. B. Lobkovsky, G. W. Coates, Chem. Commun. 2000, 2007–2008.
- 146M. Cheng, D. R. Moore, J. J. Reczek, B. M. Chamberlain, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 8738–8749.
- 147G. W. Coates, M. Cheng, US Pat. Appl., 2000, US 6,133,402 [ Chem. Abstr. 2000, 132, 152332].
- 148M. Cheng, Ph.D. Thesis, Cornell University, August 2000.
- 149D. R. Moore, M. Cheng, E. B. Lobkovsky, G. W. Coates, Angew. Chem. 2002, 114, 2711–2714;
Angew. Chem. Int. Ed. 2002, 41, 2599–2602.
10.1002/1521-3773(20020715)41:14<2599::AID-ANIE2599>3.0.CO;2-N CAS PubMed Web of Science® Google Scholar
- 150S. D. Allen, D. R. Moore, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 14 284–14 285.
- 151D. R. Moore, M. Cheng, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2003, 125, 11 911–11 924.
- 152D. R. Moore, Ph.D. Thesis, Cornell University, May 2003.
- 153S. D. Allen, D. R. Moore, E. B. Lobkovsky, G. W. Coates, J. Organomet. Chem. 2003, 683, 137–148.
- 154M. Cheng, A. B. Attygalle, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 1999, 121, 11 583–11 584.
- 155B. M. Chamberlain, M. Cheng, D. R. Moore, T. M. Ovitt, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 3229–3238.
- 156L. R. Rieth, D. R. Moore, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 15 239–15 248.
- 157M. H. Chisholm, J. C. Huffman, K. Phomphrai, J. Chem. Soc. Dalton Trans. 2001, 222–224.
- 158M. H. Chisholm, J. Gallucci, K. Phomphrai, Inorg. Chem. 2002, 41, 2785–2794.
- 159R. Eberhardt, M. Allmendinger, G. A. Luinstra, B. Rieger, Organometallics 2003, 22, 211–214.
- 160M. Zhang, L. B. Chen, B. Liu, Z. Yan, G. Qin, Z. Li, Polym. Bull. 2001, 47, 255–260.
- 161M. Zhang, L. B. Chen, G. Qin, Z. M. Li, Acta Polym. Sin. 2001, 422–424.
- 162M. Zhang, L. B. Chen, G. Qin, B. Liu, Z. Yan, Z. Li, J. Appl. Polym. Sci. 2003, 87, 1123–1128.
- 163K. Yu, C. W. Jones, Organometallics 2003, 22, 2571–2580.
- 164W. J. van Meerendonk, R. Duchateau, C. E. Koning, G. M. Gruter, Macromol. Rapid Commun. 2004, 25, 382–386.
- 165Z. W. Liu, M. Torrent, K. Morokuma, Organometallics 2002, 21, 1056–1071.
- 166M. H. Chisholm, D. Navarro-Llobet, Macromolecules 2002, 35, 2389–2392.
- 167M. H. Chisholm, D. Navarro-Llobet, Z. Zhou, Macromolecules 2002, 35, 6494–6504.
- 168S. D. Allen, G. W. Coates, unpublished results.
- 169K. Nakano, N. Kosaka, T. Hiyama, K. Nozaki, Dalton Trans. 2003, 4039–4050.
- 170D. M. Hodgson, A. R. Gibbs, G. P. Lee, Tetrahedron 1996, 52, 14 361–14 384.
- 171K. Nozaki, K. Nakano, T. Hiyama, J. Am. Chem. Soc. 1999, 121, 11 008–11 009.
- 172K. Tamao, T. Hiyama, Y. Hori (Takasago Perfumery Co., Ltd.), Jpn. Kokai Tokkyo Koho 2000256454, 2000 [ Chem. Abstr. 2000, 133, 223229].
- 173K. Nakano, K. Nozaki, T. Hiyama, Macromolecules 2001, 34, 6325–6332.
- 174K. Nakano, K. Nozaki, T. Hiyama, J. Am. Chem. Soc. 2003, 125, 5501–5510.
