Generation of Alkyl(dicarbonyl)(chloro)-ruthenium Dimers in the Ruthenium-Catalyzed Addition of Alkyl Formates to Ethylene

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 10, 1997, Pages 1092-1095

  Fabre, Sylvie ^a   Kalck, Philippe ^a   Lavigne, Guy ^b  

^a UNIVERSITÉ DE TOULOUSE   (France)

^b CNRS   (France)

Author keywords

Acylations; Alkylations; Homogeneous catalysis; Ruthenium

Indexed keywords

EID: 0030837846     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199710921     Document Type: Article

References (47)

1. a) G. Lavigne, N. Lugan, P. Kalck, J.-M. Soulié, O. Lerouge, J.-Y. Saillard, J.-F. Halet, J. Am. Chem. Soc. 1992, 114, 10669-10670;
2. b) N. Lugan, G. Lavigne, J.-M. Soulié, P. Kalck, J.-Y. Saillard, J.-F. Halet, Organometallics 1995, 14, 1713-1731.
3. For recent reviews on alkyl formates, see a) G. Jenner, Appl. Catal. A 1995, 121, 25-44; b) W. Leitner, Angew. Chem. 1995, 107, 2391-2405; Angew. Chem. Int. Ed. Engl. 1995, 34, 2207-2221.
4. For recent reviews on alkyl formates, see a) G. Jenner, Appl. Catal. A 1995, 121, 25-44; b) W. Leitner, Angew. Chem. 1995, 107, 2391-2405; Angew. Chem. Int. Ed. Engl. 1995, 34, 2207-2221.
5. For recent reviews on alkyl formates, see a) G. Jenner, Appl. Catal. A 1995, 121, 25-44; b) W. Leitner, Angew. Chem. 1995, 107, 2391-2405; Angew. Chem. Int. Ed. Engl. 1995, 34, 2207-2221.
6. For references on Ru-catalyzed hydroesterification of olefins, see a) P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual, J. Organomet. Chem. 1983, 256, 135-139; b) W. Keim, J. Becker, J. Mol. Catal. 1989, 54, 95-101; c) T. Kondo, S. Yoshii, Y. Tsuji, Y. Watanabe, ibid. 1989, 50, 31-38; d) C. Legrand, Y. Castanet, A. Mortreux, F. Petit (Atochem), Eur. Pat. Appl., 449 693 A, 1991; e) C. Legrand, Y. Castanet, A. Mortreux, F. Petit, J. Chem. Soc. Chem. Commun. 1994, 1173-1174; f) Y. Suzuki, H. Katoh, Y. Ishii, M. Hidai, J. Mol. Catal. A 1995, 95, 129-133.
7. For references on Ru-catalyzed hydroesterification of olefins, see a) P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual, J. Organomet. Chem. 1983, 256, 135-139; b) W. Keim, J. Becker, J. Mol. Catal. 1989, 54, 95-101; c) T. Kondo, S. Yoshii, Y. Tsuji, Y. Watanabe, ibid. 1989, 50, 31-38; d) C. Legrand, Y. Castanet, A. Mortreux, F. Petit (Atochem), Eur. Pat. Appl., 449 693 A, 1991; e) C. Legrand, Y. Castanet, A. Mortreux, F. Petit, J. Chem. Soc. Chem. Commun. 1994, 1173-1174; f) Y. Suzuki, H. Katoh, Y. Ishii, M. Hidai, J. Mol. Catal. A 1995, 95, 129-133.
8. For references on Ru-catalyzed hydroesterification of olefins, see a) P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual, J. Organomet. Chem. 1983, 256, 135-139; b) W. Keim, J. Becker, J. Mol. Catal. 1989, 54, 95-101; c) T. Kondo, S. Yoshii, Y. Tsuji, Y. Watanabe, ibid. 1989, 50, 31-38; d) C. Legrand, Y. Castanet, A. Mortreux, F. Petit (Atochem), Eur. Pat. Appl., 449 693 A, 1991; e) C. Legrand, Y. Castanet, A. Mortreux, F. Petit, J. Chem. Soc. Chem. Commun. 1994, 1173-1174; f) Y. Suzuki, H. Katoh, Y. Ishii, M. Hidai, J. Mol. Catal. A 1995, 95, 129-133.
9. For references on Ru-catalyzed hydroesterification of olefins, see a) P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual, J. Organomet. Chem. 1983, 256, 135-139; b) W. Keim, J. Becker, J. Mol. Catal. 1989, 54, 95-101; c) T. Kondo, S. Yoshii, Y. Tsuji, Y. Watanabe, ibid. 1989, 50, 31-38; d) C. Legrand, Y. Castanet, A. Mortreux, F. Petit (Atochem), Eur. Pat. Appl., 449 693 A, 1991; e) C. Legrand, Y. Castanet, A. Mortreux, F. Petit, J. Chem. Soc. Chem. Commun. 1994, 1173-1174; f) Y. Suzuki, H. Katoh, Y. Ishii, M. Hidai, J. Mol. Catal. A 1995, 95, 129-133.
10. For references on Ru-catalyzed hydroesterification of olefins, see a) P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual, J. Organomet. Chem. 1983, 256, 135-139; b) W. Keim, J. Becker, J. Mol. Catal. 1989, 54, 95-101; c) T. Kondo, S. Yoshii, Y. Tsuji, Y. Watanabe, ibid. 1989, 50, 31-38; d) C. Legrand, Y. Castanet, A. Mortreux, F. Petit (Atochem), Eur. Pat. Appl., 449 693 A, 1991; e) C. Legrand, Y. Castanet, A. Mortreux, F. Petit, J. Chem. Soc. Chem. Commun. 1994, 1173-1174; f) Y. Suzuki, H. Katoh, Y. Ishii, M. Hidai, J. Mol. Catal. A 1995, 95, 129-133.
11. For references on Ru-catalyzed hydroesterification of olefins, see a) P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual, J. Organomet. Chem. 1983, 256, 135-139; b) W. Keim, J. Becker, J. Mol. Catal. 1989, 54, 95-101; c) T. Kondo, S. Yoshii, Y. Tsuji, Y. Watanabe, ibid. 1989, 50, 31-38; d) C. Legrand, Y. Castanet, A. Mortreux, F. Petit (Atochem), Eur. Pat. Appl., 449 693 A, 1991; e) C. Legrand, Y. Castanet, A. Mortreux, F. Petit, J. Chem. Soc. Chem. Commun. 1994, 1173-1174; f) Y. Suzuki, H. Katoh, Y. Ishii, M. Hidai, J. Mol. Catal. A 1995, 95, 129-133.
12. 3, Rw = 0.039, R = 0.036; b) same overall geometry as for 2 [5a]; the observation of large thermal parameters affecting the β-carbon atoms of alkyl groups was consistent with a partial occupation of these sites due to the alternation of Ru-bound methyl and ethyl groups.
13. 3, R = 0.025, Rw = 0.0249. Crystallographic data for the structures of 2 and 5 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100027. Copies of the data can be obtained free of charge on application to the Director, CCDC, 12 Union road, Cambridge, CB2 1EZ, UK (fax: int. code +(1223)336-033; e-mail: deposit @chemcrys.cam.ac.uk).
14. For FSBO complexes with metals other than Ru, see a) F. A. Cotton, J. L. Eglin, S.-J. Kang, J. Am. Chem. Soc. 1992, 114, 4015-4016; b) R. Poli, J. C. Gordon, ibid. 1992, 114, 6723-6734.
15. For FSBO complexes with metals other than Ru, see a) F. A. Cotton, J. L. Eglin, S.-J. Kang, J. Am. Chem. Soc. 1992, 114, 4015-4016; b) R. Poli, J. C. Gordon, ibid. 1992, 114, 6723-6734.
16. For FSBO complexes of Ru, see a) R.-A. Sanchez-Delgado, U. Thewalt, N. Valencia, A. Andriollo, R.-L. Marquez-Silva, J. Puga, H. Schölhorn, H. P. Klein, B. Fontal, Inorg. Chem. 1986, 25, 1097-1106, and references therein; b) I. S. Thorburn, S. J. Rettig, B. R. James, ibid. 1986, 25, 234-240; c) A. M. Joshi, I. S. Thorburn, S. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198-200, 283-296; d) A. M. Joshi, K. S. MacFarlane, B. R. James, J. Organomet. Chem. 1995, 488, 161-167; e) K. Mashima, T. Hino, H. Takaya, J. Chem. Soc. Dalton Trans. 1992, 2099-2107; f) T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, H., K. Mashima, Organometallics 1996, 15, 1521-1523; g) D. Touchard, S. Guesmi, M. Bouchaib, P. Haquette, A. Daridor, P. H. Dixneuf, ibid. 1996, 15, 2579-2581.
17. For FSBO complexes of Ru, see a) R.-A. Sanchez-Delgado, U. Thewalt, N. Valencia, A. Andriollo, R.-L. Marquez-Silva, J. Puga, H. Schölhorn, H. P. Klein, B. Fontal, Inorg. Chem. 1986, 25, 1097-1106, and references therein; b) I. S. Thorburn, S. J. Rettig, B. R. James, ibid. 1986, 25, 234-240; c) A. M. Joshi, I. S. Thorburn, S. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198-200, 283-296; d) A. M. Joshi, K. S. MacFarlane, B. R. James, J. Organomet. Chem. 1995, 488, 161-167; e) K. Mashima, T. Hino, H. Takaya, J. Chem. Soc. Dalton Trans. 1992, 2099-2107; f) T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, H., K. Mashima, Organometallics 1996, 15, 1521-1523; g) D. Touchard, S. Guesmi, M. Bouchaib, P. Haquette, A. Daridor, P. H. Dixneuf, ibid. 1996, 15, 2579-2581.
18. For FSBO complexes of Ru, see a) R.-A. Sanchez-Delgado, U. Thewalt, N. Valencia, A. Andriollo, R.-L. Marquez-Silva, J. Puga, H. Schölhorn, H. P. Klein, B. Fontal, Inorg. Chem. 1986, 25, 1097-1106, and references therein; b) I. S. Thorburn, S. J. Rettig, B. R. James, ibid. 1986, 25, 234-240; c) A. M. Joshi, I. S. Thorburn, S. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198-200, 283-296; d) A. M. Joshi, K. S. MacFarlane, B. R. James, J. Organomet. Chem. 1995, 488, 161-167; e) K. Mashima, T. Hino, H. Takaya, J. Chem. Soc. Dalton Trans. 1992, 2099-2107; f) T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, H., K. Mashima, Organometallics 1996, 15, 1521-1523; g) D. Touchard, S. Guesmi, M. Bouchaib, P. Haquette, A. Daridor, P. H. Dixneuf, ibid. 1996, 15, 2579-2581.
19. For FSBO complexes of Ru, see a) R.-A. Sanchez-Delgado, U. Thewalt, N. Valencia, A. Andriollo, R.-L. Marquez-Silva, J. Puga, H. Schölhorn, H. P. Klein, B. Fontal, Inorg. Chem. 1986, 25, 1097-1106, and references therein; b) I. S. Thorburn, S. J. Rettig, B. R. James, ibid. 1986, 25, 234-240; c) A. M. Joshi, I. S. Thorburn, S. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198-200, 283-296; d) A. M. Joshi, K. S. MacFarlane, B. R. James, J. Organomet. Chem. 1995, 488, 161-167; e) K. Mashima, T. Hino, H. Takaya, J. Chem. Soc. Dalton Trans. 1992, 2099-2107; f) T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, H., K. Mashima, Organometallics 1996, 15, 1521-1523; g) D. Touchard, S. Guesmi, M. Bouchaib, P. Haquette, A. Daridor, P. H. Dixneuf, ibid. 1996, 15, 2579-2581.
20. For FSBO complexes of Ru, see a) R.-A. Sanchez-Delgado, U. Thewalt, N. Valencia, A. Andriollo, R.-L. Marquez-Silva, J. Puga, H. Schölhorn, H. P. Klein, B. Fontal, Inorg. Chem. 1986, 25, 1097-1106, and references therein; b) I. S. Thorburn, S. J. Rettig, B. R. James, ibid. 1986, 25, 234-240; c) A. M. Joshi, I. S. Thorburn, S. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198-200, 283-296; d) A. M. Joshi, K. S. MacFarlane, B. R. James, J. Organomet. Chem. 1995, 488, 161-167; e) K. Mashima, T. Hino, H. Takaya, J. Chem. Soc. Dalton Trans. 1992, 2099-2107; f) T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, H., K. Mashima, Organometallics 1996, 15, 1521-1523; g) D. Touchard, S. Guesmi, M. Bouchaib, P. Haquette, A. Daridor, P. H. Dixneuf, ibid. 1996, 15, 2579-2581.
21. For FSBO complexes of Ru, see a) R.-A. Sanchez-Delgado, U. Thewalt, N. Valencia, A. Andriollo, R.-L. Marquez-Silva, J. Puga, H. Schölhorn, H. P. Klein, B. Fontal, Inorg. Chem. 1986, 25, 1097-1106, and references therein; b) I. S. Thorburn, S. J. Rettig, B. R. James, ibid. 1986, 25, 234-240; c) A. M. Joshi, I. S. Thorburn, S. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198-200, 283-296; d) A. M. Joshi, K. S. MacFarlane, B. R. James, J. Organomet. Chem. 1995, 488, 161-167; e) K. Mashima, T. Hino, H. Takaya, J. Chem. Soc. Dalton Trans. 1992, 2099-2107; f) T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, H., K. Mashima, Organometallics 1996, 15, 1521-1523; g) D. Touchard, S. Guesmi, M. Bouchaib, P. Haquette, A. Daridor, P. H. Dixneuf, ibid. 1996, 15, 2579-2581.
22. For FSBO complexes of Ru, see a) R.-A. Sanchez-Delgado, U. Thewalt, N. Valencia, A. Andriollo, R.-L. Marquez-Silva, J. Puga, H. Schölhorn, H. P. Klein, B. Fontal, Inorg. Chem. 1986, 25, 1097-1106, and references therein; b) I. S. Thorburn, S. J. Rettig, B. R. James, ibid. 1986, 25, 234-240; c) A. M. Joshi, I. S. Thorburn, S. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198-200, 283-296; d) A. M. Joshi, K. S. MacFarlane, B. R. James, J. Organomet. Chem. 1995, 488, 161-167; e) K. Mashima, T. Hino, H. Takaya, J. Chem. Soc. Dalton Trans. 1992, 2099-2107; f) T. Ohta, Y. Tonomura, K. Nozaki, H. Takaya, H., K. Mashima, Organometallics 1996, 15, 1521-1523; g) D. Touchard, S. Guesmi, M. Bouchaib, P. Haquette, A. Daridor, P. H. Dixneuf, ibid. 1996, 15, 2579-2581.
23. 3, R = 0.028, Rw = 0.032.
24. 2] and partially characterized: K. R. Grundy, J. Jenkins, J. Organomet. Chem. 1984, 265, 77-85.
25. a) C. Bohanna, M. A. Esteruelas, F. J. Lahoz, E. Onate, L. A. Oro, Organometallics 1995, 14, 4685-4696;
26. b) W. R. Roper, G. E. Taylor, J. M. Waters, L. J. Wright, J. Organomet. Chem. 1979, 182, C46-C48;
27. c) S. M. Maddock, C. E. F. Rickard, W. Roper, L. Wright, Organometallics 1996, 15, 1793-1803;
28. d) H. Werner, M. A. Esteruelas, H. Otto, ibid. 1986, 5, 2295-2299;
29. e) R. B. Bedford, A. F. Hill, A. J. P. White, D. J. Williams, Angew. Chem. 1996, 108, 94-96; Angew. Chem. Int. Ed. Engl. 1996, 35, 95-97.
30. e) R. B. Bedford, A. F. Hill, A. J. P. White, D. J. Williams, Angew. Chem. 1996, 108, 94-96; Angew. Chem. Int. Ed. Engl. 1996, 35, 95-97.
31. a) J. T. Poulton, K. Folting, W. E. Streib, K. G. Caulton, Inorg. Chem. 1992, 31, 3190-3191;
32. b) J. T. Poulton, M. P. Sigalas, O. Eisenstein, K. G. Caulton, ibid. 1993, 32, 5490-5501.
33. a) S. D. Ittel, C. A. Tolman, A. D. English, J. P. Jesson, J. Am. Chem. Soc. 1978, 100, 7577-7585;
34. b) C. A. Tolman, S. D. Ittel, A. D. English, J. P. Jesson, ibid. 1979, 101, 1742-1751;
35. c) R. L. Pruett, R. T. Kacmarcik, Organometallics 1982, 1, 1693-1699.
36. a) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147, and references therein;
37. b) T. Yamamoto, J. Ishizu, A. Yamamoto, J. Am. Chem. Soc. 1981, 103, 6863-6869;
38. c) Bull. Chem. Soc. Jpn. 1982, 55, 623-624.
39. T. Kondo, S. Kajiya, S. Tantayanon, Y. Watanabe, J. Organomet. Chem. 1995, 489, 83-91.
40. G. Jenner, A. Ben Taleb, J. Mol. Catal. 1994, 91, 31-43.
41. a) D. L. Thorn, Organometallics 1982, 1, 197-204;
42. b) D. Milstein, J. Am. Chem. Soc. 1986, 108, 3525-3526;
43. c) C. Bianchini, M. Peruzzini, F. Vizza, F. Zanobini, J. Organomet. Chem. 1988, 348, C9-C11.
44. Notably, an intermolecular association of mononuclear methoxycarbonyl ruthenium complexes has been recently reported, see G. Süss-Fink, J.-M. Soulié, G. Rheinwald, H. Stoeckli-Evans, Y. Sazaki, Organometallics 1996, 15, 3416-3422.
45. 3) bond of the ester and condensation of the fragments; b) V. V. Grushin, Acc. Chem. Res. 1993, 26, 279-286.
46. 2 and methane or ethane (depending on the alkyl formate source), but no traces of CO, were detected by GC in the gaseous phase of the reactor once the reaction was terminated.
47. Note added in proof: In a continuatino of this work we have now found that the alkyl complex 2 can be generated (albeit less efficiently) from ethylene in the absence of alkyl formate with water as the only hydrogen source: C. Andres, S. Fabre, B. de Bonneval, G. Lavigne, P. Kalck, unpublished results.