Chromium(III) octaethylporphyrinato tetracarbonylcobaltate: A highly active, selective, and versatile catalyst for epoxide carbonylation

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11426-11435

  Schmidt, Joseph A R ^a,b   Lobkovsky, Emil B ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

^b UNIVERSITY OF TOLEDO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBONYLATION; CATALYSIS; CATALYSTS; ESTERS; ETHERS; NEGATIVE IONS; NITROGEN COMPOUNDS; PORPHYRINS; SEPARATION; SYNTHESIS (CHEMICAL);

EPOXIDES; GLYCIDYL ESTERS; LACTONES; REACTION STEREOCHEMISTRY;

ORGANIC COMPOUNDS;

ALIPHATIC COMPOUND; AMIDE; CHROMIUM DERIVATIVE; CHROMIUM OCTAETHYLPORPHYRINATOTETRACARBONYL COBALTATE; COBALT DERIVATIVE; EPOXIDE; ESTER; ETHER DERIVATIVE; GAMMA LACTONE DERIVATIVE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYST; COMPLEX FORMATION; ISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 23844542414     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051874u     Document Type: Article

References (99)

1. Pommier, A.; Pons, J. M. Synthesis 1993, 441-459.
2. Müller, H.-M.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 477-502.
3. Pommier, A.; Pons, J. M. Synthesis 1995, 729-744.
4. Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403-6434.
5. Sato, T.; Kawara, T.; Nishizawa, A.; Fujisawa, T. Tetrahedron Lett. 1980, 21, 3377-3380.
6. Normant, J. F.; Alexakis, A.; Cahiez, G. Tetrahedron Lett. 1980, 21, 935-938.
7. Arnold, L. D.; Drover, J. C. G.; Vederas, J. C. J. Am. Chem. Soc. 1987, 109, 4649-4659.
8. Schechtman, L. A.; Kemper, J. J. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1999, 40 (1), 508-509.
9. Kurcok, P.; Kowalczuk, M.; Hennek, K.; Jedlinski, Z. Macromolecules 1992, 25, 2017-2020.
10. Hori, Y.; Suzuki, Y. A.; Nishishita, T. Macromolecules 1993, 26, 5533-5534.
11. LeBorgne, A.; Pluta, C.; Spassky, N. Macromol. Rapid Commun. 1994, 15, 955-960.
12. Lenz, R. W.; Yang, J.; Wu, B.; Harlan, C. J.; Barron, A. R. Can. J. Microbiol. 1995, 41, 274-281.
13. Rieth, L. R.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 15239-15248.
14. Martin, D. P.; Williams, S. F.; Skraly, F. A. In Methods of Tissue Engineering; Atala, A., Lanza, R. P., Eds.; Academic Press: San Diego, CA, 2002.
15. Snell, K. D.; Peoples, O. P. Metab. Eng. 2002, 4, 29-40.
16. Williams, S. F.; Martin, D. P.; Horowitz, D. M.; Peoples, O. P. Int. J. Biol. Macromol. 1999, 25, 111-121.
17. Reppe, W.; Kroper, H.; Pistor, J.; Weissbarth, O. Justus Liebigs Ann. Chem. 1953, 552, 87-116.
18. Eisenmann, J. L.; Yamartino, R. L.; Howard, J. F. J. Org. Chem. 1961, 26, 2102-2104.
19. Heck, R. F. J. Am. Chem. Soc. 1963, 55, 1460-1461.
20. Direct copolymerization of CO and epoxides to give polyesters has been met with some success: (a) Furukawa, J.; Iseda, Y.; Saegusa, T.; Fujii, H. Makromol. Chem. 1965, 89, 263-268.
21. (b) Jia, L.; Ding, E.; Anderson, W. R. Chem. Commun. 2001, 1436-1437.
22. (c) Takeuchi, D.; Sakaguchi, Y.; Okasada, K. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 4530-4537.
23. (d) Allmendinger, M.; Eberhardt, R.; Luinstra, G.; Rieger, B. J. Am. Chem. Soc. 2002, 124, 5646-5647.
24. (e) Allmendinger, M.; Eberhardt, R.; Luinstra, G.; Rieger, B. Macromol. Chem. Phys. 2003, 204, 564-569.
25. (f) Lee, J. T.; Alper, H. Macromolecules 2004, 37, 2417-2421.
26. For a recent interesting advance in CO/aziridine copolymerization, see: (g) Jia, L.; Sun, H.; Shay, J. T.; Allgeier, A. M.; Hanton, S. D. J. Am. Chem. Soc. 2002, 124, 7282-7283 and references therein.
27. Drent, E.; Kragtwijk, E. (Shell Internationale Research Maatschappij B, V., Neth.) Eur. Pat. Appl. EP 577206: Chem. Abstr. 1994, 120, 191517e.
28. Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 64, 2164-2165.
29. Lee, J. T.; Thomas, P. J.; Alper, H. J. Org. Chem. 2001, 66, 5424-5426.
30. Allmendinger, M.; Eberhardt, R.; Luinstra, G. A.; Molnar, F.; Rieger, B. Z. Anorg. Allg. Chem. 2003, 629, 1347-1352.
31. Molnar, F.; Luinstra, G. A.; Allmendinger, M.; Rieger, B. Chem.-Eur. J. 2003, 9, 1273-1280.
32. Allmendinger, M.; Zintl, M.; Eberhardt, R.; Luinstra, G. A.; Molnar, F.; Rieger, B. J. Organomet. Chem. 2004, 689, 971-979.
33. Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781-2784.
34. Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1174-1175.
35. Schmidt, J. A. R.; Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Org. Lett. 2004, 6, 373-376.
36. Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. Pure Appl. Chem. 2004, 76, 557-564.
37. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
38. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938.
39. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362.
40. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
41. Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2004, 126, 2495-2500.
42. Evano, G.; Schaus, J. V.; Panek, J. S. Org. Lett. 2004, 6, 525-528.
43. Colby, E. A.; O'Brien, K. C.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 998-999.
44. Dakin, L. A.; Panek, J. S. Org. Lett. 2003, 5, 3995-3998.
45. Rodriguez, A. R.; Spur, B. W. Tetrahedron Lett. 2003, 44, 7411-7415.
46. eff = 3.87.
47. Edgell, W. F.; Yang, M. T.; Koizumi, N. J. Am. Chem. Soc. 1965, 87, 2563-2567.
48. Schore, N. E.; Ilenda, C. S.; White, M. A.; Bryndza, H. E.; Matturro, M. G.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7451-7461.
49. w = 0.137; GOF = 0.948.
50. ORTEP-3 for Windows; Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
51. Inamo, M.; Hoshino, M.; Nakajima, K.; Aizawa, S. I.; Funahashi, S. Bull. Chem. Soc. Jpn. 1995, 68, 2293-2303.
52. Inamo, M.; Nakaba, H.; Nakajima, K.; Hoshino, M. Inorg. Chem. 2000, 39, 4417-4423.
53. Inamo, M.; Nakajima, K. Bull. Chem. Soc. Jpn. 1998, 71, 883-891.
54. Nichols, P. J.; Fallon, G. D.; Moubaraki, B.; Murray, K. S.; West, B. O. Polyhedron 1993, 12, 2205-2213.
55. Oyaizu, K.; Haryono, A.; Nishimura, Y.; Yamamoto, K.; Tsuchida, E. Bull. Chem. Soc. Jpn. 1999, 72, 1781-1784.
56. Balch, A. L.; Latosgrazynski, L.; Noll, B. C.; Olmstead, M. M.; Zovinka, E. P. Inorg. Chem. 1992, 31, 1148-1151.
57. Klufers, P. Z. Kristallogr. 1983, 165, 217-226.
58. Klufers, P. Z. Kristallogr. 1984, 167, 253-260.
59. Klufers, P. Z. Kristallogr. 1984, 167, 275-286.
60. Klufers, P. Z. Kristallogr. 1984, 166, 143-151.
61. Vaughan, W. R.; Cartwright, W. F.; Henzi, B. J. Am. Chem. Soc. 1972, 94, 4978-4984.
62. Spartan '02, version 1.0.4; Wavefunction, Inc.: Irvine, CA.
63. Brown, S. P.; Bal, B. S.; Pinnick, H. W. Tetrahedron Lett. 1981, 22, 4891-4894.
64. Ikan, R.; Weinstein, V.; Ravid, U. Org. Prep. Proced. Int. 1981, 13, 59-70.
65. Koch, S. S. C.; Chamberlin, A. R. Stud. Nat. Prod. Chem. 1995, 16, 687-725.
66. Metzger, C.; Borrmann, D.; Wegler, R. Chem. Ber. 1967, 100, 1817-1823.
67. Mulzer, J.; Bruntrup, G. Angew. Chem., Int. Ed. Engl. 1979, 18, 793-794.
68. Black, T. H.; Fields, J. D. Synth. Commun. 1988, 18, 125-130.
69. Thompson, K. L.; Chang, M. N.; Chiang, Y. C. P.; Yang, S. S.; Chabala, J. C.; Arison, B. H.; Greenspan, M. D.; Hanf, D. P.; Yudkovitz, J. Tetrahedron Lett. 1991, 32, 3337-3340.
70. Reetz, M. T.; Schmitz, A.; Holdgrun, X. Tetrahedron Lett. 1989, 30, 5421-5424.
71. Winstein, S.; Buckles, R. E. J. Am. Chem. Soc. 1942, 64, 2780-2786.
72. Pigman, W.; Horton, D., Eds. The Carbohydrates: Chemistry and Biochemistry; 2nd ed.; Academic Press: New York, 1972; Vol. 1A.
73. Baba, A.; Nozaki, T.; Matsuda, H. Bull. Chem. Soc. Jpn. 1987, 60, 1552-1554.
74. Weijers, C.; Botes, A. L.; van Dyk, M. S.; de Bont, J. A. M. Tetrahedron: Asymmetry 1998, 9, 467-473.
75. Mischitz, M.; Kroutil, W.; Wandel, U.; Faber, K. Tetrahedron: Asymmetry 1995, 6, 1261-1272.
76. Davies, A. G.; Hawaii, J. A. A.; Muggleton, B.; Tse, M. W. J. Chem. Soc., Perkin Trans. 2 1981, 1132-1137.
77. Kam, S. T.; Malier, W. L.; Mai, K. X.; Barcelon-Yang, C.; Borgman, R. J.; O'Donnell, J. P.; Stampfli, H. F.; Sum, C. Y.; Anderson, W. G.; Gorczynski, R. J.: Lee, R. J. J. Med. Chem. 1984, 27, 1007-1016.
78. Glushko, L. P.; Petukhova, E. I.; Klebanskii, E. O. Zh. Organich. Khim. 1997, 33, 1527-1531.
79. Berlin, A. A.; Popova, G. L.; Makarova, T. A. Vysokomol. Soedin. 1959, 1, 962-965.
80. Edgell, W. F.; Lyford, J. Inorg. Chem. 1970, 9, 1932-1933.
81. Noels, A. F.; Herman, J. J.; Teyssie, P. J. Org. Chem. 1976, 41, 2527-2531.
82. Romo, D.; Harrison, P. H. M.; Jenkins, S. I.; Riddoch, R. W.; Park, K.; Yang, H. W.; Zhao, C.; Wright, G. D. Bioorg. Med. Chem. 1998, 6, 1255-1272.
83. Peres, R.; Lenz, R. W. Macromolecules 1993, 26, 6697-6701.
84. Sakai, N.; Ageishi, S.; Isobe, H.; Hayashi, Y.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 2000, 71-77.
85. Yang, H. W.; Zhao, C. X.; Romo, D. Tetrahedron 1997, 55, 16471-16488.
86. Crandall, J. K.; Machlede, W. H.; Sojka, S. A. J. Org. Chem. 1973, 38, 1149-1154.
87. Stille, J. K.; James, D. E. J. Organomet. Chem. 1976, 108, 401-408.
88. Tiecco, M.; Testaferri, L.; Tingoli, M.; Bartoli, D. Tetrahedron 1990, 46. 7139-7150.
89. Evans, D. F. J. Chem. Soc. 1959, 2003-2005.
90. SMART: Area-Detector Software Package: Siemens Industrial Automation, Inc.: Madison, WI, 1995.
91. SAINT: SAX Area-Detector Integration Program, version 4.024; Siemens Industrial Automation, Inc.: Madison, WI, 1995.
92. SADABS: Siemens Area Detector ABSorption Correction Program; George Sheldrick, 1996.
93. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343-350.
94. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF Program System, Technical Report of the Crystallography Laboratory; University of Nijmegen: The Netherlands, 1992.
95. Sheldrick, G. M. SHELX 97; Universität Göttingen: Göttingen, Germany, 1997.
96. -1 and p is the factor used to lower the weight of intense reflections.
97. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; The Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.2A.
98. Ibers, J. A.; Hamilton, W. C. Acta Crystallogr. 1964, 17, 781-782.
99. The synthesis, IR spectrum, boiling point, and refractive index of 46 have previously been reported: van Tamelen, E. E.; Strong, F. M.; Quarck, U. C. J. Am. Chem. Soc. 1959, 81, 750-751.