Rates and mechanism of rhodium-catalyzed [2+2+2] cycloaddition of bisalkynes and a monoalkyne

Organometallics

Volumn 28, Issue 20, 2009, Pages 6036-6043

  Dachs, Anna ^a   Torrent, Anna ^b   Pla Quintana, Anna ^b   Roglans, Anna ^a   Jutand, Anny ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b UNIVERSITY OF GIRONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION REACTIONS; CYCLIC VOLTAMMETRY; DICHLOROMETHANE; HYDROCARBONS; REACTION INTERMEDIATES;

CATALYTIC CYCLES; CONDUCTIVITY MEASUREMENTS; ELECTROCHEMICAL TECHNIQUES; INTERMEDIATE COMPLEX; OXIDATIVE COUPLINGS; RHODIUM-CATALYZED; SUBSTITUTED BENZENES; [2+2+2] CYCLOADDITION;

RHODIUM COMPOUNDS;

EID: 70350330345     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900544u     Document Type: Article

References (54)

1. For recent reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000,100,2901-2916.
2. (b) Yamamoto, Y. Curr. Org. Chem. 2005, 9, 503-519.
3. (c) Kotha, S.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741-4767.
4. (d) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307-2327.
5. (e)Gandon, V.; Aubert, C.; Malacria, M. Chem. Commun. 2006, 2209-2217.
6. (f) Tanaka, K. Synlett 2007, 1977-1993.
7. (g) Agenet, N.; Buisine, O.; Slowinski, F.; Gandon, V.; Aubert, C.; Malacria, M. Org. React. 2007, 68, 1-302.
8. (h) Varela, J. A.; Saá, C. Synlett 2008, 2571-2578.
9. (i) Shibata, T.; Tsuchikama, K. Org. Biomol. Chem. 2008, 6, 1317-1323.
10. (J) Galan, B. R.; Rovis, T. J. Angew. Chem., Int. Ed. 2009, 48, 2830-2834.
11. (a) Pla-Quintana, A.; Roglans, A.; Torrent, A.; Moreno-Mañas, M.; Benet-Buchholz, J. Organometallics 2004, 23, 2762-2767.
12. (b) Torrent, A.; González, I.; Pla-Quintana, A.; Roglans, A.; Moreno-Mañas, M.; Parella, T.; Benet-Buchholz, J. Org. Chem. 2005, 70,2033-2041.
13. (c) González, I.; Bouquillon, S.; Roglans, A.; Muzart, J. Tetrahedron Lett. 2007,48,6425-6428.
14. (d) Brun, S.; Garcia, L.; González, I.; Torrent, A.; Dachs, A.; PlaQuintana, A.; Parella, T.; .Roglans, A. Chem. Commun. 2008,4339-4341.
15. For a pioneering semiempirical study, see: (a) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M. -L; Eisenstein, O.; Jackson, S. A.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010-2023.
16. For DFT studies of the reaction mechanism of the [2+2+2] cycloadditions involving three acetylene molecules catalyzed by Co, see: (b) Hardesty, J. H.; Koemer, J. B.; Albright, T. A.; Lee, G.-Y. J. Am. Chem, Soc. 1999,121,6055-6067.
17. (c) Dahy, A. A.; Koga, N. Bull. Chem. Soc. Jpn. 2005, 78, 781-791.
18. (d) Dahy, A. A.; Suresh, C. H.; Koga, N. Bull. Chem, Soc. Jpn. 2005,78,792-803.
19. (e) Agenet, N.; Gandon, V.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. J. Am. Chem. Soc. 2007, 129, 8860-8871.
20. (f) Varela, J. A.; Saá, C. J. Organomet. Chem. 2009,694,143-149.
21. Catalyzed by Ru, see: (g) Kirchner, K.; Calhorda, M. J.; Schmid, R.; Veiros, L. F. J. Am. Chem. Soc. 2003,125,11721-11729.
22. (h) Yamamoto, Y; Arakawa, T.; Ogawa, R.; Itoh, K.J. Am. Chem. Soc. 2003,125,12143-12160.
23. (i) Schmid, R.; Kirchner, K. Eur. J. Inorg. Citem. 2004, 2609-2626.
24. (j) Dazinger, G.; TorresRodrigues, M.; Kirchner, K.; Calhorda, M. J.; Costa, P. J. J. Organomet. Chem. 2006,691,4434-4445.
25. (l) Kirchner, K. Monatsch. Chem. 2008,139, 337-348.
26. (m) Catalyzed by CpRh and InRh, see: Orian, L.; van Stolen, J. N. P.; Bickelhaupt, F. M. Organometallics 2007,26, 3816-3830.
27. Dachs, A.; Torrent, A.; Roglans, A.; Parella, T.; Osuna, S.; Sola, M. Chem. Eur. J. 2009,15, 5289-5300.
28. Selected, references: (a) Müller, E. Syntltesis 1974,761-774.
29. (b) Mague, J. T. Inorg. Chem. 1970, 9, 1610-1618.
30. (c) Mague, J. T. Inorg. Chem. 1973, 12, 2649-11654
31. (d) Gastinger, R. G.; Rausch, M. D.; Sullivan, D. A.; Palenik, G. J. J. Organomet. Chem. 1976,117,355-364.
32. (e) Iglesias, M.,; del Pino, C.; Ros, J.; García Blanco, S.; Carrera, S. M. J. Organomet. Chem, 1988,338, 89-102.
33. (f) Bianchini, C.; Caulton, K. G.; Chardon, C.; Eisenstein, O.; Folting, K.; Johnson, T. J.; Meli, A,; Peruzzini, M.; Rauscher, D. J.; Streib, W. E.; Vizza, F. J. Am. Chem. Soc. 1991, 113, 5127-5129.
34. (g) Bianchini, C.; Masi, D.; Meli, A.; Peruzzini, M.; Vacca, A. Organometallics 1991,10,636-645.
35. (h) Bianchini, C.; Meli, A.; .Peruzzini, M.; Vacca, A.; Vizza, F. Organometallics 1991,1.0,645-651.
36. (i) Rourke, J. P.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Chem. Commun. 2001,2626-2627.
37. (j) Nishiyama, H.; Niwa, E.; Inoue, T.; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574.
38. (k) Xue, P.; Sung, H. S. Y; Williams, I. D.; Jia, G. Organomet. Chem. 2006,691,1945-1953.
39. Schore, N. E. Chem. Rev. 1988,88,1081.-1119.
40. Amer, I.; Bernstein, T.; Eisen, M.; Blum, J.; Vollhardt, K. P. C. J. Mol. Catal. 1990, 60,313-321.
41. For a review on the use of electrochemistry to get kinetics data on the reactivity of organometallic complexes, see: Jutand, A. Chem, Rev. 2008, 108,2300-2347.
42. 3), at a glassy-carbon disk see: Barrière, F.; Geiger, W. E. Organometallics 2001,20, 2133-2135.
43. Osborn, J. A. Jardine, F. H.; Young, J. F.; Wilkinson, G. Inorg. Phys. Theor. (A) 1.966, 1711-1732.
44. Tolman, C.A.;Meakin,P. Z.; Lindner, D. L.: Jesson. J.P. J. Am. Chem. Soc. 1974, 96, 2762-2774.
45. (a) Bard, A. J., Faulkner, L. R. Electrochemical Methods. Fundamentals and Applications, 2nd ed.; Wiley: New York, 2001.
46. 3 (reversible) involves one electron each.
47. 13C NMR spectra when characterizing the resulting products.
48. Electrospray Ionization Mass Spectrometry, Fundamentals, Instrumentation and Applications; Cole, R. B., Ed.; Wiley-Interscience: New York, 1997.
49. (a) Santos, L. S.; Knaack, L.; Metzger, J. O.Int. J. Mass Spectrom. 2005, 246,84-104.
50. (b) Eberlin, M. N. J. Mass Spectrom. 2006,41,141-156.
51. 17 Evidence for the formation of neutral complexes 2 in dichloromethane as confirmed by conductivity measurements might seem to contrast with the ESI-MS results. However, this is not the case, as the ionic species detected by means of ESI-MSI could be formed by insource dissociation (i.e., chlorine and/or triphenylphosphine dissociation) from undetectable neutral species present in the solution.
52. For reviews on the characterization of ionic coordination compounds by conductivity measurements, see: (a) Geary, W. J. Coord. Chem. Rew. 1971, 7, 81-122.
53. (b) Jutand, A. Egr. J. Inorg. Chem. 2003,2017-2040.
54. elimt.