Biscarbene-ruthenium complexes in catalysis: Novel stereoselective synthesis of (1E,3E)-1,4-disubstituted-1,3-dienes via head-to-head coupling of terminal alkynes and addition of carboxylic acids

Journal of the American Chemical Society

Volumn 125, Issue 39, 2003, Pages 11964-11975

  Le Paih, Jacques ^a   Monnier, Florian ^a   Dérien, Sylvie ^a   Dixneuf, Pierre H ^a   Clot, Eric ^b   Eisenstein, Odile ^b  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

^b UNIV MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CHEMICAL BONDS; COMPLEXATION; RATE CONSTANTS; STEREOCHEMISTRY;

DOUBLE BONDS;

CATALYSIS;

ALKADIENE; ALKYNE; AMINO ACID DERIVATIVE; BISCARBENE; BISCARBENE RUTHENIUM COMPLEX; CARBENE; CARBENOID; CARBOXYLIC ACID; DICARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CIS TRANS ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141508975     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0349554     Document Type: Article

References (66)

1. (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
2. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
3. (c) Murahashi, S.-I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443.
4. (d) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168 and cited references.
5. (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311.
6. (b) Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1997, 507.
7. (a) Tsuji, J. Palladium Reagents and Catalysis, Innovation in Organic Synthesis; John Wiley and Sons: New York, 1995.
8. (b) Malleron, J. L.; Fiaud, J. C.; Legros, J. Y. Handbook of Palladium-Catalyzed Organic Reactions. Synthetic Aspects and Catalytic Cycles; Academic Press: New York, 1997.
9. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
10. (d) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
11. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
12. (a) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
13. (b) Mitsudo, T.-a.; Kondo, T. Synlett 2001, 309.
14. (c) Trost. B. M. Acc. Chem. Res. 2002, 35, 695.
15. (a) Dérien, S.; Ropartz, L.; Le Paih, J.; Dixneuf, P. H. J. Org. Chem. 1999, 64, 3524.
16. (b) Le Paih, J.; Dérien, S.; Özdemir, I.; Dixneuf, P. H. J. Am. Chem. Soc. 2000, 122, 7400.
17. (c) Le Paih. J.; Dérien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2001, 40, 2912.
18. (d) Trost, B. M.; Pinkerton, A. B.; Toste, F. D.; Sperrle, M. J. Am. Chem. Soc. 2001, 123, 12504.
19. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714.
20. (f) Mitsudo, T.-a.; Naruse, H.; Kondo, T.; Osaki, Y.; Watanabe, Y. Angew. Chem., Ed. Engl. 1994, 33, 580.
21. (g) Yi, C. S.; Torres-Lubian, J. R.; Liu, N.; Rheingold, A. L.; Guzei, I. A. Organometallics 1998, 17, 1257.
22. (h) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. Chem. Commun. 2000. 549.
23. (a) Yi, C. S.; Liu, N. Synlett 1999, 3, 281.
24. (b) Yi, C. S.; Torres-Lubian, J. R.; Liu, N.; Rheingold, A. L.; Guzei, I. A. Organometallics 1998, 17, 1257.
25. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; John Wiley & Sons: New York, 1992.
26. (a) Trost, B. M.; Chan, C.; Ruhter, G. J. Am. Chem. Soc. 1987, 109, 3486.
27. (b) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
28. 10b,11,13
29. (a) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275.
30. (b) Slugovc, C.; Doberer, D.; Gemel, C.; Schmid, R.; Kirchner, K.; Winkler, B.; Stelzer, F. Monatsh. Chem. 1998, 129, 221.
31. Yi, C. S.; Liu, N.; Rheingold, A. L.; Liable-Sands, L. M. Organometallics 1997, 16, 3910.
32. (a) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
33. (b) Bianchini, C.; Peruzzini, M.; Zanobini, F.; Frediani, P.; Albinati, A. J. Am. Chem. Soc. 1991, 113, 5453.
34. Matsuzaka, H.; Takagi, Y.; Ishii, Y.; Nishio, M.; Hidai, M. Organometallics 1995, 14, 2153.
35. Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604.
36. Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968.
37. Albers, M. O.; de Waal, D. J. A.; Liles, D. C.; Robinson, D. J.; Singleton, E.; Wiege, M. B. J. Chem. Soc., Chem. Commun. 1986, 1680.
38. (a) Crocker, M.; Green, M.; Nagle, K. R.; Orpen, A. G.; Neumann, H.-P.; Morton, C. E.; Schaverien, C. J. Organometallics 1990, 9, 1422.
39. (b) Crocker, M.; Dunne, B. J.; Green, M.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1991, 1589.
40. (a) Ruba, E.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Commun. 2001, 1996.
41. (b) Ruba, E.; Mereiter, K.; Schmid, R.; Kirchner, K.; Bustelo, E.; Puerta, M. C.; Valerga, P. Organometallics 2002, 21, 2912.
42. (a) Ernst, C.; Walter, O.; Dinjus, E.; Arzberger, S.; Görls, H. J. Prakt. Chem. 1999, 8, 341.
43. (b) Ernst, C.; Walter, O.; Dinjus, E. J. Organomet. Chem. 2001, 627, 249.
44. (c) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 2712.
45. (a) Le Bozec, H.; Fillaut, J.-L.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1986, 1182.
46. (b) Osborn, V. A.; Parker, M. J.; Winter, J. J. Chem. Soc., Chem. Commun. 1986, 1185.
47. Fagan, P. J.; Mahoney, W. S.; Calabrese, J. C.; Williams, I. D. Organometallics 1990, 9, 1843.
48. A preliminary account on the first evidence of this reaction was reported: Le Paih, J.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 1999, 1437.
49. 1C=C(Ph)OAc bond of 2 which shows the lower field signal of both isomers.
50. Murray, R. E. European Patent, 0351 603 A2, 1989.
51. Bach, R. D.; Woodard, R. A.; Anderson, T. J.; Glick, M. D. J. Org. Chem. 1982, 47, 3707.
52. (a) Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247.
53. (b) Doucet, H.; Höfer, J.; Derrien, N.; Bruneau, C.; Dixneuf, P. H. Bull. Soc. Chim. Fr. 1996, 133, 939.
54. Gemel, C.; Le Pensee, A.; Mauthner, K.; Schmid, R.; Kirchner, K. Monatsh. Chem. 1997, 128, 1189.
55. Rüba, E.; Mereiter, K.; Schmid, R.; Sapunov, V. N.; Kirchner, K.; Schottenberger, H.; Calhorda, M. J.; Veiros, L. F. Chem.-Eur. J. 2002, 8, 3948.
56. Jeffrey, G. A.; Saenger, W. In H-Bonding in Biological Structures; Springer: Weinheim, 1994.
57. Svensson, M.; Humbel, S.; Froesee, R. D. J.; Matsubara, T.; Sieber, S.; Morokuma, K. J. Phys. Chem. 1998, 100, 19357.
58. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck. A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, G.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.; Pittsburgh, PA, 1998.
59. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
60. (b) Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 82, 284.
61. Rappé, A. K.; Casewitt, C.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
62. Andrae, D.; Haüßermann, U.; Dolg, M.; Stoll, H.; Preuß, H. Theor. Chim. Acta 1990, 77, 123.
63. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
64. Bergner, A.; Dolg, M.; Küchle, H.; Stoll, H.; Preuß, H. Mol. Phys. 1990, 30, 1431.
65. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
66. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.