Palladium-catalyzed cyclopropanation of alkenyl silanes by diazoalkanes: Evidence for a Pd0 mechanism

Chemistry - A European Journal

Volumn 15, Issue 12, 2009, Pages 2923-2931

  Berthon Gelloz, Guillaume ^a   Marchant, Melanie ^a   Straub, Bernd F ^b   Marko, Istvan E ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Cyclization; Density functional calculations; Diazo compounds; Homogeneous catalysis; Palladium

Indexed keywords

CATALYSIS; CATALYSTS; COMPETITION; CYCLIZATION; DENSITY FUNCTIONAL THEORY; OLEFINS; PALLADIUM; PROPANE; REACTION KINETICS; SILANES; STYRENE;

ACTIVE CATALYSTS; ALKENYL; CATALYST LOADINGS; CYCLOPROPANATION; CYCLOPROPANATION REACTIONS; DENSITY FUNCTIONAL CALCULATIONS; DIASTEREOSELECTIVITIES; DIAZO COMPOUNDS; DIAZOALKANES; DIAZOMETHANE; EXPERIMENTAL OBSERVATIONS; HOMOGENEOUS CATALYSIS; LOW LOADINGS; REACTION PATHWAYS; RESTING STATE; TERMINAL ALKENES; TRANS-ISOMERS; TURN-OVER FREQUENCIES; VINYL SILANES;

PALLADIUM COMPOUNDS;

ALKENE; AZO COMPOUND; CYCLOPROPANE DERIVATIVE; DIVINYLTETRAMETHYLDISILOXANE; PALLADIUM; SILANE DERIVATIVE; SILOXANE; STYRENE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

ALKENES; AZO COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOPROPANES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PALLADIUM; SILANES; SILOXANES; STEREOISOMERISM; STYRENE; THERMODYNAMICS;

EID: 62349103436     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802052     Document Type: Article

References (68)

1. J. Pietruszka, Chem. Rev. 2003, 103, 1051.
2. J. Salaün, Top. Curr. Chem. 2000, 207, 1.
3. Z. Rappoport in The Chemistry of the Functional Groups (Ed.: S. Patai), Wiley, New York, 1987.
4. Chemistry of the Cyclopropyl Group, Vol. 2 (Ed.: Z. Rappoport), Wiley, New York, 1995.
5. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977.
6. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49.
7. M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911.
8. A. B. Charette, H. Lebel in Comprehensive Asymmetric Catalysa I-III, Vol. 2 (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 581.
9. K. M. Lydon, M. A. McKervey in Comprehensive Asymmetric Catalysis I-III, Vol.2 (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 539.
10. A. Pfaltz, in Comprehensive Asymmetric Catalysis I-III, Vol. 2 (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 513.
11. A. Pfaltz in Transition Metals for Organic Synthesis, Vol. 1 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, p. 157.
12. M. Rubina, V. Gevorgyan, Tetrahedron 2004, 60, 3129.
13. M. P. Doyle in Modern RhodiumCatalyzed Organic Reactions (Ed.: P.A. Evans), Wiley-VCH, Weinheim, 2005, p. 341.
14. R. K. Armstrong, J. Org. Chem. 1966, 31, 618.
15. R. Paulissen, A.J. Hubert, P. Teyssié, Tetrahedron Lett. 1972, 13, 1465.
16. O. Reiser in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1 (Eds.: E.-i. Negishi, A. de Meijere), Wiley-Interscience, New York, 2002, p. 1561.
17. J. Kottwitz, H. Vorbrüggen, Synthesis 1975. 636.
18. U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629.
19. A. Nakamura, T. Yoshida, M. Cowie, S. Otsuka, J. A. Ibers, J. Am. Chem. Soc. 1977, 99, 2108.
20. A. J. Anciaux, A. J. Hubert, A. F. Noels, N. Petiniot, P. Teyssié, J. Org. Chem. 1980, 45, 695.
21. M. Suda, Synthesis 1981, 714.
22. H. Abadallah, R. Gree, R. Carrie, Tetrahedron Lett. 1982, 23, 503.
23. M. P. Doyle, R. L. Dorow, W. E. Buhro, J. H. Griffin, W. H. Tamblyn, M. L. Trudell, Organometallics 1984, 3, 44.
24. Y. V. Tomilov, V. G. Bordakov, A. I. Lutsenko, S. O. Kozhinskii, I. E. Dolgii, O. M. Nefedov, Russ. Chem. Bull. 1987, 36, 1234.
25. P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815.
26. K. Shimamoto, M. Ishida, H. Shinozaki, Y. Ohfune, J. Org. Chem. 1991, 56, 4167.
27. J. Vallgårda, U. Hacksell, Tetrahedron Lett. 1991, 32, 5625.
28. I. Basnak, K. Jurkovic, G. Basnakova, Synth. Commun. 1992, 22, 773.
29. M. Nasim, V. S. Petrosyan, G. S. Zaitseva, J. Lorberth, J. Organomet. Chem. 1992, 430, 269.
30. J. Vallgårda, U. Appelberg, I. Csoregh, U. Hacksell, J. Chem. Soc. Perkin Trans. 11994, 461.
31. S. Vangveravong, D. E. Nichols, J. Org. Chem. 1995, 60, 3409.
32. G. S. Zaitseva, S. S. Karlov, A. V. Churakov, E. V. Avtomonov, J. Lorberth, D. Hertel, J. Organomet. Chem. 1996, 523, 221.
33. S. E. Denmark, R. A. Stavenger, A.-M. Faucher, J. P. Edwards, J. Org. Chem. 1997, 62, 3375.
34. J. E. A. Luithle, J. Pietruszka, Liebigs Ann. 1997, 2297.
35. J. Pietruszka, M. Widenmeyer, Synlett 1997, 977.
36. J. E. A. Luithle, J. Pietruszka, A. Witt, J. Chem. Soc. Chem. Commun. 1998, 2651.
37. J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287.
38. J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans 1 2000, 4293.
39. I. E. Marko, T. Kumamoto, T. Giard, Adv. Synth. Catal. 2002, 344, 1063.
40. E. V. Guseva, N. V. Volchkov, Y. V. Tomilov, O. M. Nefedov, Eur. J. Org. Chem. 2004, 3136.
41. O. Illa, C. Rodriguez-Garcia, C. Acosta-Silva, I. Favier, D. Picurelli, A. Oliva, M. Gomez, V. Branchadell, R. M. Ortuno, Organometallics 2007, 26, 3306.
42. F. Bernardi, A. Bottoni, G. P. Miscione, Organometallics 2001, 20, 2751.
43. C. Rodriguez-Garcia, A. Oliva, R. M. Ortuno, V. Branchadell, J. Am. Chem. Soc. 2001, 123, 6157.
44. C. Rodriguez-Garcia, Gonzalez-Bianco, A. Oliva, R. M. Ortuno, V. Branchadell, Eur. J. Inorg. Chem. 2000, 1073.
45. B. F. Straub, J. Am Chem. Soc. 2002, 124, 14195.
46. I. E. Marko, T. Giard, S. Sumida, A.-E. Gies, Tetrahedron Lett. 2002, 43, 2317.
47. N. Heureux, M. Marchant, N. Maulide, G. Berthon-Gelloz, C. Hermans, S. Hermant, E. Kiss, B. Leroy, P. Wasnaire, I. E. Markó, Tetrahedron Lett. 2005, 46, 79.
48. J. W. Fitch, D. P. Flores, J. E. George, J. Organomet. Chem. 1971, 29, 263.
49. J. W. Fitch, K. C. Chan, J. A. Froelich, J. Organomet. Chem. 1978, 160, 477.
50. V. F. Mironov, V. D. Sheludyakov, V. V. Shcherbinin, E. A. Viktorov, Zh. Obshch. Khim. 1975, 45, 1796.
51. J. Schraml, M. Grignon-Dubois, J. Dunogues, H. Jancke, G. Engelhardt, V. Chvalovsky, Collect. Czech. Chem. Commun. 1983, 79, 3396.
52. K. Hirabayashi, A. Mori, T. Hiyama, Tetrahedron Lett. 1997, 38, 461.
53. G. Berthon-Gelloz, J.-M. Schumers, G. De Bo, E. I. Marko, J. Org. Chem. 2008, 73, 4190.
54. J. W. Fitch, F. C. Willms, Inorg. Chim. Ada 1985, 97, 9.
55. P. B. Hitchcock, M. F. Läppert, N. J. W. Warhurst, Angew. Chem. 1991, 103, 439;
56. Angew. Chem. Int. Ed. Engl. 1991, 30, 438.
57. J. Krause, G. Cestaric, K.-J. Haack, K. Seevogel, W. Storm, K.-R. Pörschke, J. Am. Chem. Soc. 1999, 121, 9807.
58. Pd/DVTMS is commercially available from Umicore A.G.
59. A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
60. a) Jaguar 7.0, Schrödinger, New York, NY, 2007;
61. b) A. D. Becke, J. Chem. Phys. 1986, 84, 4524;
62. c) J.P. Perdew, Phys. Rev. B 1986, 33, 8822;
63. d) R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650;
64. e) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299;
65. f) G. Schaftenaar, J. H. Noordik, J. Comput.-Aided Mol. Design 2000, 14, 123.
66. C. Defieber, H. Grützmacher, E. M. Carreira, Angew. Chem. 2008, 120, 4558;
67. Angew. Chem. Int. Ed. 2008, 47, 4482.
68. I. J. S. Fairlamb, A. R. Kapdi, A. F. Lee, G. P. McGlacken, F. Weissburger, A. H. M. de Vries, L. Schmieder-van de Vondervoort, Chem. Eur. J. 2006, 12, 8750.