New Fischer Carbene Complexes of Rhodium(I): Preparation and 2-Cyclopentenone Ring Synthesis by Annelation to Alkynes

Journal of the American Chemical Society

Volumn 126, Issue 2, 2004, Pages 470-471

  Barluenga, José ^a   Vicente, Rubén ^a   López, Luis A ^a   Rubio, Eduardo ^a   Tomás, Miguel ^a   Álvarez Rúa, Carmen ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBENOID; CYCLOPENTENONE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; DIELS ALDER REACTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 0347717614     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038817q     Document Type: Article

References (48)

1. Recent reviews: (a) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, p 469.
2. (b) Herndon, J. W. Tetrahedron 2000, 56, 1257.
3. (c) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
4. (d) Barluenga, J.; Fañanás, F. J. Tetrahedron 2000, 56, 4597.
5. (e) Sierra, M. A. Chem. Rev. 2000, 100, 3591.
6. For palladium bis-carbene complexes proposed as the active intermediates, see: (a) Sierra, M. A.; Mancheño, M. J.; Sáez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
7. (b) Sierra, M. A.; del Amo, J. C.; Mancheño, M. J.; Gómez-Gallego, M. J. Am. Chem. Soc. 2001, 123, 851.
8. (c) Sierra, M. A.; del Amo, J. C.; Mancheño, M. J.; Gómez-Gallego, M.; Torres, M. R. Chem. Commun. 2002, 1842.
9. For the structure of a particular amino-stabilized palladium(0) carbene complex, see: Albéniz, A. C.; Espinet, P.; Manrique, R.; Pérez-Mateo, A. Angew. Chem., Int. Ed. 2002, 41, 2363.
10. For specific cyclization reactions of Cr(0) carbenes which are accelerated by Rh(I) and Cu(I), see: (a) Aumann, R.; Göttker-Schnetmann, I.; Fröhlich, R.; Meyer, O. Eur. J. Org. Chem. 1999, 2545.
11. (b) Göttker-Schnetmann, I.; Aumann, R. Organometallics 2001, 20, 346.
12. (c) Göttker-Schnetmann, I.; Aumann, R.; Bergander, K. Organometallics 2001, 20, 3574.
13. Barluenga, J.; López, L. A.; Löber, O.; Tomás, M.; García-Granda, S.; Alvarez-Rúa, C.; Borge, J. Angew. Chem., Int. Ed. 2001, 40, 3392.
14. Barluenga, J.; Barrio, P.; López, L. A.; Tomás, M.; García-Granda, S.; Alvarez-Rúa, C. Angew. Chem., Int. Ed. 2003, 42, 3008.
15. (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
16. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
17. (c) Davies, H. M. L.; Panaro, S. A. Tetrahedron 2000, 56, 4871.
18. (d) Davis, H. M. L.; Antoulinakis, E. G. J. Organomet. Chem. 2001, 617-618, 47.
19. For the synthesis of rhodium(I) zirconoxycarbene complexes, see: (a) Barger, P. T.; Bercaw, J. E. Organometallics 1984, 3, 278.
20. (b) Erker, G.; Lecht, R.; Tsay, Y.-H.; Krüger, C. Chem. Ber. 1987, 120, 1763.
21. (c) Erker, G.; Mena, M.; Hoffmann, U.; Menjón, B. Orgaometallics 1991, 10, 291.
22. Compound 3b shows a square planar coordination at the rhodium(I) center with a rhodium-carbene carbon and Rh-CO bond lengths of 1.993(9) and 1.901(10). Å. respectively. Details are given in the Supporting Information. Compounds 3.4, and 6-8 were characterized spectrospically and by elemental analysis. The structures of 4 and 6-8 were ascertained by NMR experiments (including HMQC, HMBC, COSY, and NOESY). The enol ethers, precursors of the final cyclopentenones, are detected by NMR in the reaction crude before chromatographic purification.
23. For the transfer of carbene and carbonyl ligands from a tungsten diaminocarbene complex to platinum, see: (a) Liu, S.-T.; Hsieh, T.-Y.; Lee, G.-H.; Peng, S.-M. Organomatallics 1998, 17, 993.
24. (b) Ku, R.-Z.; Huang, J.-C.; Cho, J.-Y.; Kiang, F.-M.; Reddy, K. R.; Chen, Y.-C.; Lee, K.-J.; Lee, J.-H.; Lee, G.-H.; Peng, S.-M.; Liu, S.-T. Organometallics 1999, 18, 2145.
25. Cationic complexes of Rh(I) with diaminocarbene ligands: (a) Herrmann, W. A.; Goosen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162.
26. (b) Werner, H.; Hörlin, G.; Mahr, M. J. Organomet. Chem. 1998, 551, 367.
27. (c) Buron, C.; Stelzig, L.; Gerret, O.; Gortnitzka, H.; Romanenko, V.; Bertrand, G. J. Organomet. Chem. 2002, 664, 70.
28. For a cationic Rh(I) diarylcarbene complex, see: (d) Bleuel, E.; Weberndörfer, B.; Werner, H. J. Organomet. Chem. 2001, 617-618, 502.
29. For cationic Rh(I) vinylidene and allenylidene complexes, see: (e) Windmüller, B.; Nürnberg, O.; Wolf, J.; Werner, H. Eur. J. Inorg. Chem. 1999, 613.
30. The [3 + 2] cyclization of alkynes to metal carbenes leading to substituted cyclopentadienes has been reported for the particular case of group 6 β-aminoalkenyl(alkoxy)carbene complexes. See: (a) de Meijere, A.; Shirmer, H.; Duetsch, M. Angew. Chem., Int. Ed. 2000, 39, 3964.
31. (b) Aumann, R. Eur. J. Org. Chem. 2000, 17.
32. (c) Reference 3.
33. Electron-poor alkynes react with alkenyl(alkoxy)carbenes of chromium yielding mixtures of bicyclic lactones (Halban-White cyclization) and phenols depending on the nature of the activating group: (a) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
34. (b) Brandvold, T. A.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1991, 113, 5459.
35. (c) Brandvold, T. A.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 1645.
36. (d) Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D.; Rheingold, A. L. Organometallics 1998, 17, 4298.
37. For an interesting discussion on the intramolecular reaction of diazo derivatives and unactivated alkynes catalyzed by rhodium(II). see: Padwa, A. J. Organomet. Chem. 2001, 617-618, 3.
38. For previous examples of 1-metalla-1,3-dienes in [4 + 21 cycloadditions. see: (a) Trost, B. M.; Hashmi, S. K. J. Am. Chem. Soc. 1994, 116, 2183.
39. (b) Hoffmann, M.; Buchert, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 876.
40. (c) Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182.
41. (d) Barluenga, J.; López, S.; Flórez, J. Angew. Chem., Int. Ed. 2003, 42, 231.
42. For an excellent theoretical study on 1.2- and 1.4-cycloaddition reactions of rhodiabenzene complexes, see: (e) Iron, M. A.; Martin, J. M. L.; van der Boom, M. E. J. Am. Chem. Soc. 2003, 125, 11702.
43. The vinyl rhodiacyclobutene formation/1,3-rearrangement sequence might be also acceptable. See: Padwa, A.; Kassir, J. M.; Xu. S. L. J. Org. Chem. 1997, 62, 1642. A carbene/alkyne insertion mechanism apparently would not explain the observed regiochemistry.
44. In a different approach, 3-methoxycyclopentenones result from neutral alkynes and cyclopropyl(methoxy)carbenes of chromium. See: Herndon, J. W.; Zu, J. Org. Lett. 1999, 1, 15 and references therein.
45. Reviews: (a) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003. 42, 1800.
46. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, p 703.
47. For an intermolecular reaction involving electron-poor and strained alkenes, see, respectively: (c) Ahmar, M.; Antras, F.; Cazes, B. Tetrahedron Lett. 1999, 40, 5503.
48. (d) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. Org. Lett. 2001, 3, 3193.