Quantitative determination of the regioselectivity of nucleophilic addition to η 3-propargyl rhenium complexes and direct observation of an equilibrium between η 3-propargyl rhenium complexes and rhenacyclobutenes

Organometallics

Volumn 28, Issue 1, 2009, Pages 123-131

  Casey, Charles P ^a   Boiler, Timothy M ^a   Samec, Joseph S M ^a   Reinert Nash, John R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEX 1; DIRECT OBSERVATIONS; DISSOCIATIVE MECHANISMS; H NMR SPECTRUM; INDIRECT MEASUREMENTS; LOW TEMPERATURES; NUCLEOPHILIC ADDITIONS; PROPARGYL; QUANTITATIVE DETERMINATIONS; RATE RATIOS; RHENIUM COMPLEXES;

ACETYLENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS COMPOUNDS; REGIOSELECTIVITY; RHENIUM;

RHENIUM COMPOUNDS;

EID: 61949363045     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800739j     Document Type: Article

References (101)

1. Reviews: (a) Chen, J.-T. Coord. Chem. Rev. 1999, 190-192, 1143.
2. (b) Kurosawa, H.; Ogoshi, S. Bull. Chem. Soc. Jpn. 1998, 71, 973.
3. (c)Doherty, S.; Corrigan, J. F.; Carty, A. J.; Sappa, E. Adv. Organomet. Chem. 1995, 37, 39.
4. (d) Wojcicki, A. New J. Chem. 1994, 18, 61.
5. Gotzig, J.; Otto, H.; Werner, H. J. Organomet. Chem. 1985, 287, 247.
6. (a) Krivykh, V. V.; Taits, E. S.; Petrovskii, P. V.; Struchov, Y. T.; Yanovski, A. I. Mendeleev Commun. 1991, 103.
7. (b) Gusev, O. V.; Krivykh, V. V.; Rubezhov, A. Z. Organomet. Chem. USSR 1991, 4, 233.
8. (a) Casey, C. P.; Yi, C. S. J. Am. Chem. Soc. 1992, 114, 6597.
9. (b) Casey, C. P.; Selmeczy, A. D.; Nash, J. R.; Yi, C. S.; Powell, D. R.; Hayashi, R. K. J. Am. Chem. Soc. 1996, 118, 6698.
10. (a) Blosser, P. W.; Schimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1993, 12, 1993.
11. (b) Huang, T.-M.; Chen, J.-T.; Lee, G.-H.; Wang, Y. J. Am. Chem. Soc. 1993, 115, 1170.
12. (c) Huang, T.-M.; Hsu, R.-H.; Yang, C.-S.; Chen, J.-T.; Lee, G.-H.; Wang, Y. Organometallics 1994, 13, 3657.
13. (d) Ogoshi, S.; Tsutsumi, K.; Kurosawa, H. J. Organomet. Chem. 1995, 493, C19.
14. (e) Baize, M. W.; Blosser, P. W.; Plantevin, V.; Schimpff, D. G.; Gallucci, J. C.; Wojcicki, A. Organometallics 1996, 15, 164.
15. (a) Blosser, P. W.; Gallucci, J. C.; Wojcicki, A. J. Am. Chem. Soc. 1993, 115, 2994.
16. (b) Gordon, G. J.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1997, 1045.
17. Weng, W.; Arif, A. M.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 891.
18. Stang, P. J.; Crittell, C. M.; Arif, A. M. Organometallics 1993, 12, 4799.
19. Nishida, T.; Ogoshi, S.; Tsutsumi, K.; Fukunishi, Y.; Kurosawa, H. Organometallics 2000, 19, 4488.
20. Casey, C. P.; Nash, J. R.; Yi, C. S.; Selmeczy, A. D.; Chung, S.; Powell, D. R.; Hayashi, R. K. J. Am. Chem. Soc. 1998, 120, 722.
21. 3- propargyl intermediate. However, kinetic attack at the central propargyl carbon might be reversible. Tsutsumi, K.; Yabukami, T.; Fujimoto, K.; Kawase, T.; Morimoton, T.; Kakiuchi, K. Organometallics 2003, 22, 2996.
22. Tsai, F.-Y.; Hsu, R.-H.; Huang, T.-M.; Chen, J.-T.; Lee, G.-H.; Wang, Y. J. Organomet. Chem. 1996, 520, 85.
23. (a) Baize, M. W.; Furilla, J. L.; Wojcicki, A. Inorg. Chim. Acta 1994, 223, 1.
24. (b) Baize, M. W.; Plantevin, V.; Gallucci, J. C.; Wojcicki, A. Inorg. Chim. Acta 1995, 235, 1.
25. (c) Su, C.-C.; Chen, J.-T.; Lee, G.-H.; Wang, Y. J. Am. Chem. Soc. 1994, 116, 4999.
26. (d) Plantevin, V.; Blosser, P. W.; Gallucci, J. C.; Wojcicki, A. Organometallics 1994, 13, 3651.
27. (a) For reviews, see: Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
28. (b) Ohno, H. Chem. Pharm. Bull. 2005, 53, 1211.
29. (c) Labrosse, J.-R.; Lhoste, P.; Sinou, D. J. Org. Chem. 2001, 66, 6634.
30. Ohno, H.; Okanao, A.; Kosaka, S.; Tsukamoto, K.; Ohata, M.; Ishihara, K.; Maeda, H.; Tanaka, T.; Fujii, N. Org. Lett. 2008, 10, 1171.
31. Yoshida, M.; Murao, T.; Sugimoto, K.; Ihara, M. Synlett., 2007, 575.
32. Another interesting synthetic application that involves propargyl complexesisthe palladium-catalyzeddeoxygenation of propargyl formates.Radinov, R.; Hutchings, S. D. Tetrahedron Lett. 1999, 40, 8955.
33. (a) Casey, C. P.; Vosejpka, P. C.; Askham, F. R. J. Am. Chem. Soc. 1990, 112, 3713.
34. (b) Casey, C. P.; Vosejpka, P. C.; Gavney, J. A., Jr. J. Am. Chem. Soc. 1990, 112, 4083.
35. 3 on the solvent.
36. The intriguing possibility of an associative mechanism for rear-rangement of a metallacyclobutene was explored by studying rearrangements involving 1,2-bis(diphenylphosphino)ethane ligands, where the associative mechanism would be more likely with the possibility of intramolecular attack by a second phosphine. Even with diphos ligands, the dissociative mechanism is strongly favored. See Supporting Information.
37. -1.
38. 2-alkyne complex from the initial phosphine concentration. Errors in estimation are considerable, and only very approximate equilibrium constants were obtained.
39. (a) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, UK, 1982; Vol. 8, Chapter 57.
40. (b) Tsuji, J. Tetrahedron 1986, 42, 4361.
41. (c) Trost, B. M; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
42. (d) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
43. (e) Trost, B. M. J. Org. Chem. 2004, 69, 5813.
44. (a) Ephritikhine, M.; Green, M. L. H.; Mackenzie, R. E. J. Chem. Soc., Chem. Commun. 1976, 619.
45. (b) Ephritikhine, M.; Francis, B. R.; Green, M. L. H.; Mackenzie, R. E.; Smith, M. J. J. Chem. Soc, Dalton Trans. 1977, 1131.
46. (c) Adam, G. J. A.; Davies, S. G.; Ford, K. A.; Ephritikhine, M.; Todd, P. F.; Green, M. L. H. J. Mol. Catal. 1980, 8, 15.
47. (d) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7272.
48. (e) McGhee, W. D.; Bergman, R. G. J. Am. Chem. Soc 1985, 107, 3388.
49. (f) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346.
50. (g) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420.
51. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
52. (i) Tjaden, E. B.; Stryker, J. M. Organometallics 1992, 11, 16.
53. (j) Tjaden, E. B.; Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1992, 114, 1100.
54. (k) Schwiebert, K. E.; Stryker, J. M. Organometallics 1993, 12, 600.
55. Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1993, 115, 2083.
56. (m) Review of metallacyclobutenes: Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241.
57. (a) Hegedus, L. S.; Darlington, W. H.; Russell, C. E. J. Org. Chem. 1980, 45, 5193.
58. (b) Carfagna, C.; Maniani, L.; Musco, A.; Sallese, G.; Santi, R. J. Org. Chem. 1991, 56, 3924.
59. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. Organometallics 1991, 10, 3956.
60. (d) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 234.
61. (e)Wilde, A.; Otte, A. R.; Hoffmann, H. M. R. J. Chem. Soc, Chem. Commun. 1993, 615.
62. (f) Formica, M.; Musco, A.; Pontellini, R.; Linn, K.; Mealli, C. J. Organomet. Chem. 1993, 448, C6.
63. (g) Carfagna, C.; Galarini, R.; Linn, K.; López, J. A.; Mealli, C.; Musco, A. Organometallics 1993, 12, 3019.
64. (h) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 100.
65. (i) Satake, A.; Nakata, T. J. Am. Chem. Soc. 1998, 120, 10391.
66. (j) Satake, A.; Koshino, H.; Nakata, T. Chem. Lett. 1999, 49.
67. (k) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420.
68. Grigg, R.; Korders, M. Eur. J. Org. Chem. 2001, 4, 707.
69. (a) Ohe, K.; Matsuda, H.; Morimoto, T.; Ogoshi, S.; Chatani, N.; Murai, S. J Am. Chem. Soc. 1994, 116, 4125.
70. (b) Castaño, A. M.; Aranyos, A.; Szabó, K. J.; Bäckvall, J.-E. Angew. Chem., Int. Ed. Engl. 1995, 34, 2551.
71. (c) Tsai, F.-Y.; Chen, H.-W.; Chen, J.-T.; Lee, G.H.; Wang, Y. Organometallics 1997, 16, 822.
72. (d) Aranyos, A.; Szabó, K. J.; Castaño, A. M.; Bãckvall, J.-E. Organometallics 1997, 16, 1058.
73. (e) Organ, M. G.; Miller, M. Tetrahedron Lett. 1997, 38, 8181.
74. (f) Organ, M. G.; Miller, M.; Konstantinou, Z. J. Am. Chem. Soc. 1998, 120, 9283.
75. (g) Kadota, J.; Komori, S.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1999, 64, 7523.
76. (h) Kadota, J.; Katsuragi, H.; Fukumoto, Y.; Murai, S. Organometallics 2000, 19, 979.
77. (i)Organ, M. G.; Arvanitis, E. A.; Hynes, S. J. J. Org. Chem. 2003, 68, 3918.
78. (a) Suzuki, T.; Fujimoto, H. Inorg. Chem. 1999, 38, 370.
79. (b) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995.
80. (c) Aranyos, A.; Szabó, K. J.; Castaño, A. M.; Bäckvall, J.-E. Organometallics 1997, 16, 1058.
81. (d) Ward, T. R. Organometallics 1996, 15, 2836.
82. (e) Carfagna, C.; Galarini, R.; Linn, K.; Lopez, J. A.; Mealli, C.; Musco, A. Organometallics 1993, 12, 3019.
83. (f) Curtis, M. D.; Eisenstein, O. Organometallics 1984, 3, 887.
84. (g) Davies, S. G.; Green, M. L. H.; Mingos, D. M. P. Tetrahedron 1978, 34, 3047.
85. (a) Kollmar, M.; Goldfuss, B.; Reggelin, M.; Rominger, F.; Helmchen, G. Chem.-Eur. J. 2001, 7, 4913.
86. (b) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716.
87. (c) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934.
88. (d) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015.
89. (e) Hagelin, H.; Åkermark, B.; Norrby, P. O. Chem.-Eur. J. 1999, 5, 902.
90. Carfagna, C.; Deeth, R. J.; Green, M.; Mahon, M. F.; Mclnnes, J. M.; Pellegrini, S.; Woolhouse, C. B. J. Chem. Soc, Dalton Trans. 1995, 3975.
91. Graham, J. P.; Wojcicki, A.; Bursten, B. E. Organometallics 1999, 18, 837.
92. Hall, M. B.; Fenske, R. F. Inorg. Chem. 1972, 11, 768.
93. Density functional theory (DFT) has been established as an excellent method for calculations involving organometallic compounds.
94. (a) Ziegler, T. Chem. Rev 991, 91, 651.
95. (b) Ziegler, T. Can. J. Chem. 1995, 73, 743.
96. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Adres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E. 2; Gaussian, Inc.: Pittsburgh, PA, 1995.
97. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz P.; Komaromi, I.; Gomperts, R.; 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.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A. 9; Gaussian, Inc.: Pittsburgh, PA, 1998.
98. (a) Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 4.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1996.
99. (b) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
100. 2(+.091)-C(+0.357)-CH(+0.005).
101. Labrosse, J.-R.; Lhoste, P.; Delbecq, F.; Sinou, D. Eur. J. Org. Chem. 2003, 2813.