Synthesis and characterization of alkyllanthanum biphenolate complexes as catalysts for hydroamination/cyclization and hydrosilylation

European Journal of Inorganic Chemistry

Volumn , Issue 20, 2004, Pages 4091-4101

  Gribkov, Denis V ^a   Hampel, Frank ^a   Hultzsch, Kai C ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Asymmetric catalysis; Hydroamination; Hydrosilylation; Lanthanum; O ligands

Indexed keywords

CHELATION; DIMERS; HYDROSILYLATION; LANTHANUM COMPOUNDS; LIGANDS; SINGLE CRYSTALS; STYRENE; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

ALKYL COMPLEXES; ASYMMETRIC CATALYSIS; CYCLIZATIONS; DIASTEREOSELECTIVITIES; HOMOCHIRAL DIMERS; HYDROAMINATIONS; HYDROSILYLATIONS; O LIGANDS; PHENOLATE GROUPS; ]+ CATALYST;

CATALYST ACTIVITY;

1 HEXENE; 2,2 DIMETHYLPENT 4 ENYLAMINE; ALKENE DERIVATIVE; DIMER; LANTHANUM; NORBORNENE DERIVATIVE; PENTYLAMINE; PHENOL DERIVATIVE; STYRENE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; HYDROSILYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TEMPERATURE; X RAY DIFFRACTION;

EID: 8144220210     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200400265     Document Type: Article

References (111)

1. H. Yasuda, Top. Organomet. Chem. 1999, 2, 255-283.
2. Z. Hou, Y. Wakatsuki, Coord. Chem. Rev. 2002, 231, 1-22.
3. G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161-2185.
4. [5-12]
5. T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703.
6. M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105-4108; Angew. Chem. Int. Ed. 2001, 40, 3983-3985.
7. M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105-4108; Angew. Chem. Int. Ed. 2001, 40, 3983-3985.
8. J. J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization from Hydroamination to Hydrozirconation (A. Togni, H. Grützmacher, Eds.), Wiley-VCH: Weinheim, 2001, pp. 91-141.
9. J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795-813.
10. M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579-1594.
11. F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104-114.
12. I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935-946.
13. P. W. Roesky, T. E. Müller. Angew. Chem. 2003, 115, 2812-2814; Angew. Chem. Int. Ed. 2003, 42, 2708-2710.
14. P. W. Roesky, T. E. Müller. Angew. Chem. 2003, 115, 2812-2814; Angew. Chem. Int. Ed. 2003, 42, 2708-2710.
15. M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275-294.
16. M. A. Giardello, V. P. Conticello, L. Brard, M. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241-10254.
17. M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283-292.
18. Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295-9306.
19. Y. Li, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 1757-1771.
20. V. M. Arredondo, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1998, 720, 4871-4872.
21. A. T. Gilbert, B. L. Davis, T. J. Emge, R. D. Broene, Organometallics 1999, 75, 2125-2132.
22. V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1999, 727, 3633-3639.
23. G. A. Molander, E. D. Dowdy, J. Org. Chem. 1999, 64, 6515-6517.
24. G. A. Molander, E. D. Dowdy, S. K. Pack, J. Org. Chem. 2001, 66, 4344-4347.
25. J.-S. Ryu, T. J. Marks, F. E. McDonald, Org. Lett. 2001, 3, 3091-3094.
26. J.-S. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12584-12605.
27. S. Hong, A. M. Kawaoka, T. J. Marks, J. Am. Chem. Soc. 2003, 725, 15878-15892.
28. M. R. Douglass, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 2001, 725, 10221-10238.
29. A. M. Kawaoka, M. R. Douglass, T. J. Marks, Organometallics 2003, 22, 4630-4632.
30. G. A. Molander, E. C. Dowdy, Top. Organomet. Chem. 1999, 2, 119-154.
31. T. Sakakura, H.-J. Lautenschlager, M. Tanaka, J. Chem. Soc., Chem. Commun. 1991, 40-41.
32. G. A. Molander, M. Julius, J. Org. Chem. 1992, 57, 6347-6351.
33. S.-Y. Onozawa, T. Sakakura, M. Tanaka, Tedrahedron Lett. 1994, 35, 8177-8180.
34. G. A. Molander, P. J. Nichols, J. Am. Chem. Soc. 1995, 117, 4415-4416.
35. P.-F. Fu, L. Brard, Y. Li, T. J. Marks, J. Am. Chem. Soc. 1995, 777, 7157-7168.
36. G. A. Molander, W. H. Retsch, Organometallics 1995, 14, 4570-4575.
37. G. A. Molander, P. J. Nichols, J. Org. Chem. 1996, 61, 6040-6043.
38. G. A. Molander, J. Winterfeld, J. Organomet. Chem. 1996, 524, 275-279.
39. G. A. Molander, W. H. Retsch, J. Am. Chem. Soc. 1997, 119, 8817-8825.
40. H. Schumann, M. R. Keitsch, J. Winterfeld, S. Mühle, G. A. Molander, J. Organomet. Chem. 1998, 559, 181-190.
41. G. A. Molander, E. C. Dowdy, B. C. Noll, Organometallics 1998, 77, 3754-3758.
42. G. A. Molander, E. C. Dowdy, J. Org. Chem. 1998, 63, 3386-3396.
43. H. Schumann, M. R. Keitsch, J. Demtschuk, G. A. Molander, J. Organomet. Chem. 1999, 552, 70-82.
44. G. A. Molander, C. P. Corrette, J. Org. Chem. 1999, 64, 9697-9703.
45. G. A. Molander, M. H. Schmitt, J. Org. Chem. 2000, 65, 3767-3770.
46. A. R. Muci, J. E. Bercaw, Tedrahedron Lett. 2000, 41, 7609-7612.
47. T. I. Gountchev, T. D. Tilley, Organometallics 1999, 18, 5661-5667.
48. A. A. Trifonov, T. P. Spaniol, J. Okuda, Organometallics 2001, 20, 4869-4874.
49. Y. Horino, T. Livinghouse, Organometallics 2004, 23, 12-14.
50. K. N. Harrison, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 9220-9221.
51. E. A. Bijpost, R. Duchateau, J. H. Teuben, J. Mol. Catal. A 1995, 95, 121-128.
52. G. A. Molander, D. Pfeiffer, Org. Lett. 2001, 3, 361-363.
53. H. Schumann, J. A. Meese-Marktscheffel, L. Esser, Chem. Rev. 1995, 95, 865-986.
54. F. T. Edelmann, Angew. Chem. 1995, 107, 2647-2669; Angew. Chem. Int. Ed. Engl. 1995, 34, 2466-2488.
55. F. T. Edelmann, Angew. Chem. 1995, 107, 2647-2669; Angew. Chem. Int. Ed. Engl. 1995, 34, 2466-2488.
56. F. T. Edelmann, D. M. M. Freckmann, H. Schumann, Chem. Rev. 2002, 702, 1851-1896.
57. W. E. Piers, D. J. H. Emslie, Coord. Chem. Rev. 2002, 233-234, 131-155.
58. M. R. Bürgstein, H. Berberich, P. W. Roesky, Organometallics 1998, 77, 1452-1454.
59. Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tedrahedron Lett. 2001, 42, 2933-2935.
60. M. R. Bürgstein, H. Berberich, P. W. Roesky, Chem. Eur. J. 2001, 7, 3078-3085.
61. Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797-3799; Angew. Chem. Int. Ed. 2002, 41, 3645-3647.
62. Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797-3799; Angew. Chem. Int. Ed. 2002, 41, 3645-3647.
63. P. N. O'Shaughnessy, P. D. Knight, C. Morton, K. M. Gillespie, P. Scott, Chem. Commun. 2003, 1770-1771.
64. D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796-4810.
65. Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560-9561.
66. P. N. O'Shaughnessy, P. Scott, Tedrahedron: Asymmetry 2003, 14, 1979-1983.
67. S. Hong, S. Tian, M. V. Metz, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 14768-14783.
68. J. Collin, J.-D. Daran, E. Schulz, A. Trifonov, Chem. Commun. 2003, 3048-3049.
69. D. V. Gribkov, K. C. Hultzsch, Chem. Commun. 2004, 730-731.
70. K. C. Hultzsch, F. Hampel, T. Wagner, Organometallics 2004, 23, 2601-2612.
71. [68-69].
72. S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev. 2002, 702, 2227-2302.
73. K. Mikami, M. Terada, H. Matsuzawa, Angew. Chem. 2002, 114, 3704-3722; Angew. Chem. Int. Ed. 2002, 41, 3554-3571.
74. K. Mikami, M. Terada, H. Matsuzawa, Angew. Chem. 2002, 114, 3704-3722; Angew. Chem. Int. Ed. 2002, 41, 3554-3571.
75. M. A. Giardello, V. P. Conticello, L. Brard, M. Sabat, A. L. Rheingold, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10212-10240.
76. K. C. Hultzsch, T. P. Spaniol, J. Okuda, Organometallics 1997, 16, 4845-4856.
77. J. C. Yoder, M. W. Day, J. E. Bercaw, Organometallics 1998, 17, 4946-4958.
78. J. Eppinger, PhD Dissertation, Technische Universität, München, 1999.
79. [65]
80. 2(Biphen) is commercially available from Strem Chemicals, Inc. in enantiopure form. This ligand has been successfully employed in asymmetric ring-closing metathesis reactions, see: R. R. Schrock, A. H. Hoveyda, Angew. Chem. 2003, 115, 4740-4782; Angew. Chem. Int. Ed. 2003, 42, 4592-4633.
81. 2(Biphen) is commercially available from Strem Chemicals, Inc. in enantiopure form. This ligand has been successfully employed in asymmetric ring-closing metathesis reactions, see: R. R. Schrock, A. H. Hoveyda, Angew. Chem. 2003, 115, 4740-4782; Angew. Chem. Int. Ed. 2003, 42, 4592-4633.
82. J. B. Alexander, R. R. Schrock, W. M. Davis, K. C. Hultzsch, A. H. Hoveyda, J. H. Houser, Organometallics 2000, 19, 3700-3715.
83. C. J. Schaverien, N. Meijboom, A. G. Orpen, J. Chem. Soc., Chem. Commun. 1992, 124-126.
84. One should note that in contrast to the Biphen ligand system employed in our study, Schaverien's biphenolate complexes can only be synthesized in racemic form. The 3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2, 2′-diol ligand cannot form atropisomers due to lack of sterically congesting substituents in the 6- and 6′-positions.
85. P. B. Hitchcock, M. F. Lappert, R. G. Smith, R. A. Bartlett, P. P. Power, J. Chem. Soc., Chem. Commun. 1988, 1007-1008.
86. P. L. Arnold, L. S. Natrajan, J. J. Hall, S. J. Bird, C. Wilson, J. Organomet. Chem. 2002, 647, 205-215.
87. R. Anwander, Top. Curr. Chem. 1996, 179, 149-245.
88. C. Runschke, G. Meyer, Z. Anorg. Allg. Chem. 1997, 623, 1493.
89. W. J. Evans, R. E. Golden, J. W. Ziller, Inorg. Chem. 1991, 30, 4963-4968.
90. L.-W. Yang, S. Liu; E. Wong, S. J. Rettig, C. Orvig, Inorg. Chem. 1995, 34, 2154-2178.
91. H. van der Heijden, C. J. Schaverien, A. G. Orpen, Organometallics 1989, 8, 255-258.
92. C. J. Schaverien, Adv. Organomet. Chem. 1994, 36, 283-362.
93. W. T. Klooster, L. Brammer, C. J. Schaverien, P. H. M. Budzelaar, J. Am. Chem. Soc. 1999, 727, 1381-1382.
94. R. D. Shannon, Acta Crystallogr., Sect. A 1976, 32, 751-767.
95. In fact, bis(trimethylsilyl)methyl- and bis(trimethylsilyl)amido- lanthanum binaphtholate complexes show identical catalytic activity: D. V. Gribkov, K. C. Hultzsch, unpublished results.
96. J. Eppinger, M. Spiegler, W. Hieringer, W. A. Herrmann, R. Anwander, J. Am. Chem. Soc. 2000, 722, 3080-3096.
97. R. R. Fraser, T. S. Mansour, S. Savard, J. Org. Chem. 1985, 50, 3232-3234.
98. [62-66]
99. Because of the inferior enantioselectivities observed in the hydroamination reactions using catalysts (R,R)-4 and (R)-5, the enantiomeric excess of silanes 19 and 23a was not determined.
100. K. C. Hultzsch, P. Voth, K. Beckerle, T. P. Spaniol, J. Okuda, Organometallics 2000, 19, 228-243.
101. C. J. Schaverien, Organometallics 1994, 13, 69.
102. The formation of higher aggregated species such as trimers or tetramers seems to be conceivable, as we believe that it is very likely that the dimeric μ-phenolate cage of (R,R)-4 remains intact during the catalytic cycle.
103. Y. Tamaru, M. Hojo, H. Higashimura, Z.-I. Yoshida, J. Am. Chem. Soc. 1988, 770, 3994-4002.
104. H. O. House, L. F. Lee, J. Org. Chem. 1976, 41, 863-869.
105. K. Harding, S. R. Burks, J. Org. Chem. 1981, 46, 3920-3922.
106. P. M. Smith, E. J. Thomas, J. Chem. Soc., Perkin Trans. 1 1998, 3541-3556.
107. "Collect" data collection software, Nonius B. V., 1998.
108. "Scalepack" data processing software: Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, (Macromolecular Crystallography, Part A), 307.
109. G. M. Sheldrick, SHELX-97, Program for the refinement of crystal structures, University of Göttingen, 1997.
110. D. T. Cromer, J. T. Waber, in International Tables for X-ray Crystallography (Eds.: J. A. Ibers, W. C. Hamilton), Kynoch, Birmingham, England, 1974.
111. L. J. Farrugia, Ortep-3 for Windows, J. Appl. Crystallogr. 1997, 30, 565.