Triphenylphosphane-modified cobalt catalysts for the selective carbonylation of ethyl diazoacetate

Organometallics

Volumn 29, Issue 17, 2010, Pages 3837-3851

  Ungvári, Neszta ^a   Fördos, Eszter ^a   Balogh, János ^a   Kégl, Tamás ^a   Párkányi, László ^b   Ungváry, Ferenc ^a  

^a UNIVERSITY OF PANNONIA   (Hungary)

^b CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC PRESSURE; CARBON MONOXIDE; CARBONYLATION; CATALYSTS; COBALT; DICHLOROMETHANE; ETHANOL; ORGANIC POLYMERS;

ACTIVE CATALYST; CARBONYLATION REACTIONS; CATALYST PRECURSORS; CATALYTIC CYCLES; CO CONCENTRATIONS; COBALT CATALYST; COBALT COMPLEXES; DICHLOROMETHANE SOLUTIONS; DIETHYL MALONATES; ETHYL DIAZOACETATE; INTERMEDIARY FORMATION; PRECATALYSTS; RADICAL PAIR; REUSABLE CATALYSTS; TURNOVER FREQUENCY; [CARBONYL;

COBALT COMPOUNDS;

EID: 84961978933     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100480v     Document Type: Article

References (63)

1. Tidwell, T. T. Ketenes, 2 nd ed.; Wiley: Hoboken, NJ, 2006.
2. Tidwell, T. T. Eur. J. Org. Chem. 2006, 563-576
3. Ungvári, N.; Ungváry, F. Carbonylation of diazoalkanes. In Modern Carbonylation Methods; Kollár, L., Ed.; Wiley-VCH: Weinheim, Germany, 2008; Chapter 8, pp 199 - 221.
4. Ungvári, N.; Kégl, T.; Ungváry, F. J. Mol. Catal. A: Chem. 2004, 219, 7-11
5. Tuba, R.; Ungváry, F. J. Mol. Catal. A: Chem. 2003, 203, 59-67
6. Fördo″s, E.; Tuba, R.; Párkányi, L.; Kégl, T.; Ungváry, F. Eur. J. Org. Chem. 2009, 1994-2002
7. Ungvári, N.; Fördos, E.; Kégl, T.; Ungváry, F. Inorg. Chim. Acta 2010, 363, 2016 - 2028.
8. Bor, G.; Markó, L. Chem. Ind. 1963, 912-913
9. Szabó, P.; Fekete, L.; Bor, G.; Nagy-Magos, Z.; Markó, L. J. Organomet. Chem. 1968, 12, 245-248
10. Comely, A. C.; Gibson, S. E.; Hales, N. J.; Johnstone, C.; Stevenazzi, A. Org. Biomol. Chem. 2003, 1, 1959-1968
11. Hieber, W.; Freyer, W. Chem. Ber. 1958, 91, 1230-1234
12. Tuba, R.; Fördo″s, E.; Ungváry, F. J. Mol. Catal. A: Chem. 2005, 236, 113-118
13. Vohler, O. Chem. Ber. 1958, 91, 1235-1238
14. Comely, A. C.; Gibson (née Thomas), S. E.; Hales, N. J. Chem. Commun. 1999, 2075-2076
15. Comely, A. C.; Gibson (née Thomas), S. E.; Hales, N. J. Chem. Commun. 2000, 305-306
16. Shriver, D. F. The Manipulation of Air-Sensitive Compounds; Krieger: Malabar, FL, 1982.
17. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4 th ed.; Butterworth-Heinemann: Oxford, U.K., 1996.
18. Willard, H. H.; Merritt, L. L., Jr.; Dean, J. A.; Settle, F. A., Jr. Instrumental Methods of Analysis, 6 th ed.; Wadsworth: Belmont, CA, 1981; p 206.
19. Szabó, P.; Markó, L.; Bor, G. Chem. Technol. (Leipzig) 1961, 13, 549-550
20. Edgell, W. F.; Lyford, J., IV Inorg. Chem. 1970, 9, 1932-1933
21. Winzenburg, M. L. Ph.D. Thesis, University of Minnesota, 1979; Appendix A, p 152.
22. Ruff, J. K.; Schlienz, W. J. Inorg. Synth. 1974, 15, 84-90
23. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
24. Stevens, W. J.; Basch, H.; Krauss, M. J. Chem. Phys. 1984, 81, 6026-6033
25. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261
26. http://classic.chem.msu.su/gran/gamess/index.html.
27. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc., Wallingford, CT, 2004.
29. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161
30. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129
31. -1 is always present (see Figure S1 in the Supporting Information), which is, however, absent in hexane (8, 9) or THF (10) solutions.
32. Ungvári, N.; Fördo″s, E.; Kégl, T.; Ungváry, F. Inorg. Chim. Acta 2009, 362, 1333-1342
33. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 619-635
34. Galamb, V.; Pályi, G.; Cser, F.; Furmanova, M. G.; Struchkov, Y. T. J. Organomet. Chem. 1981, 209, 183-195
35. Pályi, G.; Alberts, K.; Bartik, T.; Boese, R.; Fráter, G.; Herberich, T.; Herfurth, A.; Kriebel, C.; Sorkau, A.; Tschorner, C. M.; Zucchi, C. Organometallics 1996, 15, 3253-3255
36. Bencze, L.; Szabó, M.; J.; Szilágyi, R. K.; Boese, R.; Zucchi, C.; Pályi, G. In Fundamentals of Life; Pályi, G.; Zucchi, C.; Caglioti, L., Eds.; Elsevier: Paris, 2002; pp 451 - 471.
37. Szabó, M.; Szilágyi, R.; Bencze, L.; Boese., R.; Zucchi, C.; Caglioti, L.; Pályi, G. Enantiomer 2000, 5, 549-559
38. Zucchi, C.; Boese., R.; Alberts, K.; Herbrich, T.; Tóth, G.; Bencze, L.; Pályi, G. Eur. J. Inorg. Chem. 2001, 2297-2304
39. Zucchi, C.; Tiddia, S.; Boese., R.; Tschoerner, C. M.; Bencze, L.; Pályi, G. Chirality 2001, 13, 458-464
40. Zucchi, C.; Turrini, D.; Boese., R.; Bencze, L.; Kurdi, R.; Caglioti, L.; Pályi, G. Can. J. Chem. 2005, 83, 882-893
41. Staudinger, H.; Becker, H. Ber. Bunsen-Ges. Phys. Chem. 1927, 50, 1016-1024
42. Vogler, A.; Kunkely, H. Organometallics 1988, 7, 1449-1450
43. Ungváry, F.; Wojcicki, A. J. Am. Chem. Soc. 1987, 109, 6848-6849
44. Jonasson, A.; Persson, O.; Rasmussen, P. J. Chem. Eng. Data 2000, 45, 642-646
45. Magee, M. P.; Li, H.-Q.; Morgan, O.; Hersh, W. H. Dalton Trans. 2003, 387-394
46. Cargill, R. W., Ed. IUPAC Solubility Data Series; Pergamon Press: Oxford, U.K., 1990; Vol. 43 (Carbon Monoxide), p 166.
47. Payne, M. W.; Leussing, D. L.; Shore, S. G. J. Am. Chem. Soc. 1987, 109, 617-618
48. Albright, T. A.; Freeman, W. J.; Schweizer, E. J. Org. Chem. 1976, 41, 2716-2720
49. Pedro, F. M.; Santos, A. M.; Baratta, W.; Kühn, F. E. Organometallics 2007, 26, 302-309
50. Sacco, A. Gazz. Chim. Ital. 1963, 93, 542-548
51. Atwood, J. D. Inorg. Chem. 1987, 26, 2918-2920
52. Zhen, Y. Q.; Feighery, W. G.; Atwood, J. D. J. Am. Chem. Soc. 1991, 113, 3616-3618
53. Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 4669-4683
54. Kochi, J. K.; Bockman, T. M. Adv. Organomet. Chem. 1991, 33, 51-124
55. Wei., C. H.; Bockman, T. M.; Kochi, J. K. J. Organomet. Chem. 1992, 428, 85-97
56. Kochi, J. K. Adv. Phys. Org. Chem. 1994, 29, 185-272 and references therein
57. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998; pp 62 - 66.
58. Ellis, J. E.; Barger, P. T.; Winzenburg, M. L.; Warnock, G. F. J. Organomet. Chem. 1990, 383, 521-530
59. Geoffroy, G. L.; Bassner, S. L. Adv. Organomet. Chem. 1988, 28, 1-83
60. Ungváry, F.; Gallucci, J.; Wojcicki, A. Organometallics 1991, 10, 3053-3062
61. Huo, C. F.; Li, Y. W.; Wu, G. S.; Beller, M.; Jiao, H. J. Phys. Chem. A 2002, 106, 12161-12169
62. Fachinetti, G.; Funaioli, T. Angew. Chem., Int. Ed. Engl. 1992, 31, 1596-1599
63. Dartiguenave, M.; Menu, M. J.; Deydier, E.; Dartiguenave, Y.; Siebald, H. Coord. Chem. Rev. 1998, 178-180, 623-663