Intermolecular hydroamination of terminal alkynes catalyzed by organoactinide complexes. Scope and mechanistic studies

Organometallics

Volumn 20, Issue 24, 2001, Pages 5017-5035

  Straub, Thomas ^a   Haskel, Ariel ^a   Neyroud, Tal Gueta ^a   Kapon, Moshe ^a   Botoshansky, Mark ^a   Eisen, Moris S ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

INTERMOLECULAR HYDROAMINATION; ORGANOACTINIDE COMPLEXES; REGIOSELECTIVITY;

AMINATION; CATALYSIS; CATALYSTS; CHEMICAL BONDS; DIMERS; ISOMERIZATION; MECHANICAL PROPERTIES; MOLECULAR DYNAMICS; POLYMERIZATION; REACTION KINETICS; SINGLE CRYSTALS; X RAY DIFFRACTION ANALYSIS;

ORGANOMETALLICS;

EID: 0035956453     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010434i     Document Type: Article

References (138)

1. (a) Anwander, R.; Herrman, W. A. Top. Curr. Chem. 1996, 179, 1.
2. (b) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247.
3. (c) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
4. (d) Anwander, R. In In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.: VCH Publishers: New York, 1996; Vol. 2, p 866.
5. (e) Molander, G. A. Chemtracs: Org. Chem. 1998, 11, 237.
6. (a) Edelmann, F. T.; Gun'ko, Y. K. Coord. Chem. Rev. 1997, 165, 163.
7. (f) Ephritikhine, M. New. J. Chem. 1992, 16, 451.
8. Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283.
9. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Chapter 2
10. (a) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486.
11. (b) Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 524, 275.
12. (c) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
13. (d) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765.
14. Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705.
15. Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
16. (a) Heeres, H. J.; Heeres, A.; Teuben, J. H. Organometallics 1990, 9, 1508.
17. (b) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045.
18. (c) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909.
19. (d) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980.
20. (e) Jeske, G.; Schock, L. E.; Swepson, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091.
21. (f) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51.
22. Fu, P.-F.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 10747.
23. Yang, X.; Seyam, A. M.; Fu, P.-F.; Marks, T. J. Macromolecules 1994, 27, 4625.
24. (a) Molander, G. A.; Retsch, W. H. Organometallics 1995, 14, 4570.
25. (b) Sakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40.
26. (c) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157.
27. (d) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347.
28. (e) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
29. (a) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, 1992; p 35.
30. (b) Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824.
31. (a) Anwander, R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W., Eds.; VCH: Weinheim, Germany, 1997; Vol. 2, p 866.
32. (b) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121.
33. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
34. Jia, L.; Yang, X.; Seyam, A. M.; Albert I. D. L.; Fu, P.-F.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 7900.
35. Koo, K.; Fu, P.-F.; Marks, T. J. Macromolecules 1999, 32, 981.
36. Fendrick, C. M.; Schertz, L. D.; Day, V. W. J.; M. T. J. Am. Chem. Soc. 1988, 7, 1828.
37. (a) Smith, G. M.; Carpenter, J. D.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 6805.
38. (b) Bruno, J. W.; Smith, G. M.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 40.
39. Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. and references therein.
40. Haskel, A.; Wang, J. Q.; Straub, T.; Neyroud, T. G.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3025.
41. Wang, J. Q.; Dash, A. K.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. Organometallics 1999, 18, 2407.
42. Haskel, A.; Straub, T.; Dash, A. K.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3014.
43. (a) Wang, J. X.; Dash, A. K.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. J. Organomet. Chem., in press
44. (b) Dash, A. K.; Wang, J. X.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. J. Organomet. Chem., in press.
45. Dash, A. K.; Wang, J. Q.; Eisen, M. S. Organometallics 1999, 18, 4724.
46. 3 to acetylene is estimated (AM1-semi-empirical calculations) to be ∼15 kcal/mol more exothermic than that to ethylene.
47. (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
48. (b) Taube, R. In In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996; p 507.
49. (c) Roundhill, D. M. Chem. Rev. 1992, 92, 1.
50. (d) Hegedus, L. S.; Angew. Chem., Int. Ed. Engl. 1988, 27, 1113.
51. (e) Gasc, M. B.; Lattes, A.; Perie, J. J. Tetrahedron 1983, 39, 703.
52. (f) Bäckvall, J.-E. Acc. Chem. Res. 1983, 16, 335.
53. (a) Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917.
54. (b) Narita, T.; Yamaguchi, T.; Tsuruta, T. Bull. Chem. Soc. Jpn. 1973, 46, 3825.
55. (c) Narita, T.; Imai, N.; Tsuruta, T. Bull. Chem. Soc. Jpn. 1973, 46, 1242.
56. (d) Howk, B. W.; Little, E. L.; Scott, S. L.; Whitman, G. M. J. Am. Chem. Soc. 1954, 76, 1899.
57. Einstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1981, 103, 4308.
58. (a) Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Herwig, J.; Müller, T. E.; Thiel, O. R. Chem. Eur. J. 1999, 5, 1306.
59. (b) Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E. Eur. J. Inog. Chem. 1999, 7, 1121.
60. (c) Müller, T. E.; A.-K., P. J. Chem. Soc., Dalton Trans. 1999, 583.
61. (d) Kadota, I.; Shibuya, A.; Lutete, L. M.; Yamamoto, Y. J. Org. Chem. 1998, 64, 4570.
62. (e) Müller, T. E. Tetrahedron Lett. 1998, 39, 5961.
63. (f) Dorta, R.; Egli, P.; Zürcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857.
64. (g) Beller, M.; Eichberger, M.; Trauthwein, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2225.
65. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584.
66. (i) Brunet, J.-J.; Commenges, G.; Neibecker, D.; Philippot, K. J. Organomet. Chem. 1994, 469, 221.
67. (j) Seligson, A. L.; Trogler, A. L. Organometallics 1993, 12, 744.
68. (k) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738.
69. (l) Müller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A.-K.; Walter, E.; Yan, Y.-K. Organometallics 2000, 19, 170.
70. (m) Vogels, C. M.; Hayes, P. G.; Shaver, M. P.; Westcott, S. A. Chem. Commun. 2000, 51.
71. (n) Burling, S.; D., F. L.; Messerle, B. A. Organometallics 2000, 19, 87.
72. (o) McGrane, P. L.; Livinghouse, T. J. J. Am. Chem. Soc. 1993, 115, 11485.
73. (p) McGrane, P. L.; Livinghouse, T. J. J. Org. Chem. 1992, 57, 1323.
74. (q) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. J. Am. Chem. Soc. 1992, 114, 5459.
75. (r) Senn, H. M.; Blöchl, P. E.; Togni, A. J. Am. Chem. Soc. 2000, 122, 4098.
76. (a) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 1999, 38, 3389.
77. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
78. (a) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705.
79. (b) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
80. (c) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 8729.
81. (a) Tian, S.; Arredondo, V. M.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1896, 18, 2568.
82. (b) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1998, 63, 8983.
83. (c) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1999, 64, 6515.
84. (d) Gagnèe, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
85. (e) Andrew, G. T.; Davis, B. L.; Emge, T. J.; Broene, R. D. Organometallics 1999, 18, 2125.
86. Li Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757.
87. (a) Buergstein, M. R.; Berberich, H.; Roesky, P. W. Organometallics 1998, 17, 1452.
88. (b) Li, Y.; Fu, P.-F.; Marks, T. J. Organometallics 1994, 13, 439.
89. Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770.
90. (a) Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633.
91. (b) Arredondo, V. M.; McDonald, F. E. J. Am. Chem. Soc. 1998, 120, 4871.
92. (c) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. Organometallics 1999, 18, 1949.
93. Haggin, J. Chem. Eng. News 1993, 17 (22), 23.
94. In the case of terminal alkynes, the intermolecular alkyne oligomerization process are faster than alkyne hydroamination and dominates the catalytic chemistry. Heeres, H. J.; Nijhoff, J.; Tueben, J. H. Organometallics 1993, 12, 2609.
95. Straub, T.; A., H.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364.
96. For a preliminary report see ref 39.
97. Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773-3775.
98. Fagan, P. J. M., J. M.; Maatta, E. A.; Seyam, A. M.; Marks, T. J. J. Am. Chem. Soc. 1981, 103, 6650.
99. Solladie-Cavallo, A.; Bencheqroun, M.; Bonne, F. Synth. Commun. 1993, 23, 1683.
100. Tan, W.; He-Line, W.; Bourdieu, C.; Foucaud, A. Tetrahedron 1990, 46, 6715.
101. (a) Audit, M.; Davoust, D.; Goasdoue, N.; Platzer, N. Magn. Reson. Chem. 1985, 23, 33.
102. (b) Yamamoto, Y.; Nakada, T.; Nemoto, H. J. Am. Chem. Soc. 1992, 114, 121.
103. Allen, M.; Roberts, J. Can. J. Chem. 1981, 59, 451.
104. Steven, C.; Kimpe, N. J. Org. Chem. 1993, 58, 132.
105. Philips; CONTROL PROGRAM, program package for data collection; Philips Eindhoven (1973).
106. Hornstra & Stubbe, 1973; Goldberg, 1990. PROCN, program for data reduction; Philips Eindhoven (1973)
107. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
108. Sheldrick, G. M. SHELXL97, Program for the Refinement of Crystal Structures; University of Gottingen: Germany, 1997.
109. ORTEP, TEXRAY Structure Analysis Package; Molecular Structure Corporation: 3200 Research Forest Drive, The Woodlands, TX 77381, 1999.
110. DIFABS: Walker, N.; Stuart. Acta Crystallogr. 1983, A39, 158. An empirical program for absorption corrections.
111. DIRDIF92: 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.
112. teXsan: Crystal Structure Package: Molecular Structure Corporation: The Woodlands, TX, 1985 and 1992.
113. All toxic materials were disposed in accordance with Prudent Practices for Disposal of Chemicals from Laboratories; National Academy Press: Washington, DC, 1983.
114. Warner, B. P.; Scott, B. L.; Burns, C. J. Angew. Chem., Int. Ed. 1998, 37, 1007.
115. Arney, D. S.; Burns, C. J. J. Am. Chem. Soc. 1995, 117, 9448.
116. (a) Eigenbrot, C. W.; Raymond, K. N., Jr. Inorg. Chem. 1982, 21, 2653.
117. (b) Dutters, M. R.; Day, V. M.; Marks, T. J. J. Am. Chem. Soc. 1984, 106, 2907.
118. (c) Cramer, R. E.; Roth, S.; Edelmann, F.; Bruck, M. A.; Cohn, K. C.; Gilje, J. W. Organometallics 1989, 8, 1192.
119. (d) Cramer, R. E.; Roth, S.; Gilje, J. W. Organometallics 1989, 8, 2327.
120. Straub, T. R., G.; Frank, W.; Eisen, M. S. J. Chem. Soc., Dalton Trans. 1996, 2541.
121. (a) Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
122. (b) Spirlet, M. R.; Rebizant, J.; Apostolidis, C.; Kanellakopulos, B. Acta Crystallogr. 1992, C48, 2135.
123. (a) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; Academic Press: New York, 1980; Vol. 2.
124. Hitchock, P. B.; Lappert, M. F.; Liu, D.-S. J. Chem. Soc., Chem. Commun. 1994, 1699.
125. Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707.
126. Eisen, M. S.; Straub, T.; Haskel, A. J. Alloys Compd. 1998, 271, 116.
127. This type of equilibrium has also been observed in organolanthanide chemistry in the presence of amines, (a) Gagnè, M. R.; Brard, L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
128. (b) Gagnè, M.; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C.; Marks, T. J. Organometallics 1992, 11, 2003.
129. The same rate law is observed for the corresponding organothorium complex.
130. Elschenbroich, C.; Salzer, A. Organometallics, 1st ed.; VCH; Weinheim, Germany, 1989; Chapters 15 and 17.
131. ORTEP, TEXRAY Structure Analysis Package; Molecular Structure Corporation: 3200 Research Forest Drive, The Woodlands, TX 77381, 1999.
132. 3C≡CH. Different polarizations were found for both groups, showing the large effect of the substituent on the alkyne sp-carbon atoms. This electronic effect is believed to be responsible for the similar stereochemistry addition of TMSC≡CH to both organoactinides: (a) Stockis, A.; Hoffman, R. J. Am. Chem. Soc. 1980, 102, 2952.
133. (b) Apeloig, Y, Stanger, A. J. Am. Chem. Soc. 1985, 107, 2806.
134. (c) Allen, A. D.; Krishnamunti, R.; Surya Prakash, G. K.; Tidwell, T. T. J. Am. Chem. Soc. 1990, 112, 1291.
135. (d) Apeloig, Y.; Biton, R.; Abu-Freih, A. J. Am. Chem. Soc. 1993, 115, 2522.
136. (e) Frey, J.; Schottland, E.; Rappoport, Z.; Bravo-Zhivotovskii, D.; Nakash, M.; Botshansky, M.; Kaftory, M.; Apeloig, Y. J. Chem. Soc., Perkin Trans. 2 1994, 2555.
137. Manuscript in preparation.
138. Since amine is always present in solution, a base-catalyzed mechanism can be proposed for such a rearrangement. The lack of ratio sensitivity among the E and Z isomers for the different solvents at the different temperatures (thf, toluene) indicates a preferential concerted reaction, Miller, B. In Advanced Organic Chemistry, Reactions and Mechanism; Prentice Hall: NJ, 1988; Chapters 4-7.