Catalyst screening by electrospray ionization tandem mass spectrometry: Hofmann carbenes for olefin metathesis

Chemistry - A European Journal

Volumn 7, Issue 21, 2001, Pages 4621-4632

  Volland, Martin August Otfried ^a   Adlhart, Christian ^b   Kiener, Christoph Alexander ^a   Chen, Peter ^b   Hofmann, Peter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b ETH ZURICH   (Switzerland)

Author keywords

Carbene ligands; High throughput screening; Mass spectrometry; Metathesis; Ruthenium

Indexed keywords

CATALYSTS; CHELATION; DIMERS; IONIZATION; MASS SPECTROMETRY; MONOMERS; POLYMERIZATION; RUTHENIUM; SYNTHESIS (CHEMICAL);

ELECTROSPRAY IONIZATIONS;

OLEFINS;

ALKENE; CARBENE; CARBENOID; HALOGEN; LIGAND; PHOSPHORUS DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; DISSOCIATION; MASS SPECTROMETRY; METHODOLOGY; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035813830     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011105)7:21<4621::AID-CHEM4621>3.0.CO;2-C     Document Type: Article

References (90)

1. A general review of screening for catalysts: B. Jandeleit, H. W. Turner, T. Uno, J. A. M. van Beck, W. H. Weinberg, CATTECH 1998, 2, 101.
2. H. Burges, H. J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. 1996, 108, 192;
3. Angew. Chem. Int. Ed. Engl. 1996, 35, 220;
4. S. M. Senkan, Nature 1998, 394, 350.
5. S. Caravieilhes, C. de Bellefon, N. Tanchoux Catal. Today 2001, 66, 145.
6. B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776;
7. Angew. Chem. Int. Ed. Engl. 1996, 35, 1668;
8. T. R. Boussie, C. Coutard, H. Turner, V. Murphy, T. S. Powers, Angew. Chem. 1998, 110, 3472;
9. Angew. Chem. Int. Ed. 1998, 37, 3272.
10. A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J. 2001, 7, 3236;
11. M. T. Reetz, M. H. Becker, M. Liebl, A. Fürstner, Angew. Chem. 2000, 112, 1294;
12. Angew. Chem. Int. Ed. 2000, 39, 1236;
13. S. J. Taylor, J. P. Morken, Science 1998, 280, 267;
14. M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. 1998, 110, 2792;
15. Angew. Chem. Int. Ed. 1998, 37, 2644.
16. M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987;
17. Angew. Chem. Int. Ed. 1999, 38, 937;
18. O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366.
19. K. Mikami, R. Angelaud, K. L. Ding, A. Ishii, A. Tanaka, N. Sawada, K. Kudo, M. Senda, Chem. Eur. J. 2001, 7, 730.
20. C. Adlhart, C. Hinderling, H. Baumann, P. Chen, J. Am. Chem. Soc. 2000, 122, 8204.
21. C. Hinderling, C. Adlhart, P. Chen, Angew. Chem. 1998, 108, 2831;
22. Angew. Chem. Int. Ed. 1998, 37, 2685.
23. C. Adlhart, P. Chen, Helv. Chim. Acta 2000, 83, 2192.
24. C. Hinderling, D. A. Plattner, P. Chen, Angew. Chem. 1997, 109, 272;
25. Angew. Chem. Int. Ed. Engl. 1997, 36, 243;
26. C. Hinderling, D. Feichtinger, D. A. Plattner, P. Chen, J. Am. Chem. Soc. 1997, 119, 10793;
27. D. Feichtinger, D. A. Plattner, Angew. Chem. 1997, 109, 1796;
28. Angew. Chem. Int. Ed. Engl. 1997, 36, 1718;
29. D. Feichtinger, D. A. Plattner, P. Chen, J. Am. Chem. Soc. 1998, 120, 7175.
30. a) S. M. Hansen, F. Rominger, M. Metz, P. Hofmann, Chem. Eur. J. 1999, 5, 557;
31. b) S. M. Hansen, M. A. O. Volland, F. Rominger, F. Eisenträger, P. Hofmann, Angew. Chem. 1999, 111, 1360;
32. Angew. Chem. Int. Ed. 1999, 38, 1273;
33. c) M. A. O. Volland, B. F. Straub, I. Gruber, F. Rominger, P. Hofmann, J. Organomet. Chem. 2001, 617/ 618, 288.
34. J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus, Jr., A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 791.
35. P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 110.
36. a) Z. Wu, S. T. Nguyen, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1995, 117, 5503;
37. b) E. L. Dias, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1997, 119, 3887.
38. S. Chang, H, L. Jones C. Wang, L. M. Henling, R. H. Grubbs, Organometallics 1998, 17, 3460.
39. a) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9136;
40. b) E. L. Dias, R. H. Grubbs, Organometallics 1998, 17, 2758.
41. T. Weskamp, W. C. Schattenmann, M. Spiegier, W. A. Herrmann, Angew. Chem. 1998, 110, 2631;
42. Angew. Chem. Int. Ed. 1998, 37, 2490 (Corrigendum: Angew. Chem. 1999, 111, 277; Angew. Chem. Int. Ed. 1998, 38, 262).
43. a) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674;
44. b) T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573;
45. Angew. Chem. Int. Ed. 1999, 38, 2416;
46. c) M; Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247;
47. d) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953.
48. M. S. Sanford, M. Ulman, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 749.
49. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18.
50. For representative reviews see: T. J. Katz, Adv. Organomet. Chem. 1978, 16, 283;
51. N. Calderon, J. P. Lawrence, E. A. Ofstead, Adv. Organomet. Chem. 1979, 17, 449;
52. R. H. Grubbs, W. Tumas, Science 1989, 243, 907.
53. a) A. Fürstner, in Topics in Organometallic Chemistry, Vol. 1, Springer, Berlin, 1998;
54. b) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124;
55. Angew. Chem. Int. Ed. Engl. 1997, 36, 2037;
56. c) A. Fürstner, Angew. Chem. 2000, 112, 3140;
57. Angew. Chem. Int. Ed. 2000, 39, 3012.
58. a) S. T. Nguyen, L. K. Johnson, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 3974;
59. b) Z. Wu, A. D. Benedicto, R. H. Grubbs, Macromolecules 1993, 26, 4975;
60. R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413.
61. P. Hofmann, M. A. O. Volland, S. M. Hansen, F. Eisenträger, J. Gross, K. Stengel; J. Organomet. Chem. 2000, 606, 88.
62. J-L. Hérisson, Y. Chauvin, Makromol. Chem. 1971, 141, 161.
63. C. Adlhart, M. A. O. Volland, P. Hofmann, P. Chen, Helv. Chim. Acta 2000, 83, 3306.
64. Normalization pressure for 1-butene: 15.2 mTorr; for norbornene: 16.3 mTorr; for ethyl vinyl ether: 6.2 mTorr; for propyl vinyl ether: 5.7 mTorr.
65. abs). Relative rates (or relative adduct to reactant ratios) are normalized to one species within the same column and are not comparable within rows.
66. 2] this is found in the X-ray structure: P. Hofmann, M. A. O. Volland, unpublished results.
67. 3: 182°, (from: C A. Tolman, Chem. Rev. 1977, 77, 313).
68. J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, p. 280.
69. T. S. Lowry, K. S. Richardson, Theory and Mechanism in Organic Chemistry, 2nd ed., Harper Row, New York, 1981, Chapter 2.
70. It should be noted that a strict comparability of gas- and solution-phase results may be hampered, since solvent effects and solution-phase preequilibria are explicitly excluded in the gas phase, in which only the "naked" catalytically active species is investigated.
71. -1.[38]
72. [38]
73. a) W. Stüer, J. Wolf, H. Werner, Angew. Chem. 1998, 110, 3603;
74. Angew. Chem. Int. Ed. 1998, 37, 3421;
75. b) P. Gonzáles-Herrero, B. Weberndörfer, K. Ilg, J. Wolf, H. Werner, Angew. Chem. 2000, 112, 3392;
76. Angew. Chem. Int. Ed. 2000, 39, 3266.
77. a) M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.5, Gaussian, Pittsburgh PA, 1998;
78. b) LANL2DZ Basis Set: P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299;
79. c) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 284;
80. d) Geometries were fully optimized and analyzed by frequency calculations: for all minima NIMAG = 0, for transition states NIMAG = 1).
81. "Zur Komplexchemie und Metallorganik des Rutheniums: Der Weg zu neuen Katalysatoren für die Olefinmetathese": S. M. Hansen, Ph.D. Thesis, 1999, Heidelberg.
82. P. Liere, V. Steiner, K. R. Jennings, R. E. March, J. C. Tabet, Int. J. Mass. Spectrom. 1997, 167, 735.
83. a) H. H. Karsch, Z. Naturforsch. Teil B 1983, 38, 1027;
84. b) H. Heiss, P. Hofmann, (BASF AG) DE 41347772 A, 1992 [Chem. Abstr. 1992, 117, 171685].
85. K.-R. Pörschke, C. Pluta, B. Proft, F. Lutz, K. Krüger, Z. Naturforsch. Teil B 1993, 48, 608.
86. a) Prepared according to standard literature procedures; ligand is also available from Sigma-Aldrich Fine Chemicals;
87. b) Avocado Research Chemicals Ltd.
88. c) Sigma-Aldrich Fine Chemicals;
89. d) Strem Chemicals.
90. T. E. Wilhelm, T. R. Belderrain, S. N. Brown, R. H. Grubbs, Organometallics 1997, 16, 3867.