Ruthenium/TFA-catalyzed coupling of activated secondary propargylic alcohols with cyclic 1,3-diones: Furan versus pyran ring formation

Journal of Organic Chemistry

Volumn 73, Issue 15, 2008, Pages 5852-5858

  Cadierno, Victorio ^a   Díez, Josefina ^a   Gimeno, José ^a   Nebra, Noel ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

RUTHENIUM; RUTHENIUM COMPOUNDS;

CATALYTIC SYSTEMS; CATALYZED COUPLING; CHEMICAL EQUATIONS; PROPARGYLIC ALCOHOLS; RING FORMATION; RUTHENIUM (IV) COMPLEXES;

CHEMICAL REACTIONS;

ALCOHOL DERIVATIVE; ALLYL COMPOUND; BENZOFURAN DERIVATIVE; CARBONYL DERIVATIVE; CYCLOALKENE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; FERROCENE DERIVATIVE; KETONE DERIVATIVE; PYRAN DERIVATIVE; RUTHENIUM COMPLEX; TRIFLUOROACETIC ACID;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CROSS COUPLING REACTION; CYCLIZATION; ISOMERIZATION; MOLECULAR SIZE; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS; X RAY DIFFRACTION;

ALKYNES; BENZENE; CATALYSIS; CYCLIZATION; CYCLOPENTANES; FURANS; MOLECULAR STRUCTURE; PROPANOLS; PYRANS; RUTHENIUM; TRIFLUOROACETIC ACID;

EID: 48249141067     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800726u     Document Type: Article

References (65)

1. See, for example: (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
2. (b) Heaney, H.; Ahn, J. S. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., ; Rees, C. W., ; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1996; Vol. 2, p 297.
3. (c) Friedrichsen, W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., ; Rees, C. W., ; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1996; Vol. 2, p. 351.
4. (d) Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., ; Rees, C. W., ; Scriven, E. F. V. Eds.; Elsevier: Oxford, 1996; Vol. 2, p 395.
5. (e) Pozharskii, A. F.; Soldatenkov, A. T.; Katritzky, A. R. In Heterocycles in Life and Society; John Wiley & Sons: Chichester, 1997.
6. (f) Wong, H. N. C.; Yu, P.; Yick, C.-Y. Pure Appl. Chem. 1999, 71, 1041.
7. (g) Lee, H.-K.; Chan, K.-F.; Hui, C.-W.; Yim, H.-K.; Wu, X.-W.; Wong, H. N. C. Pure Appl. Chem. 2005, 77, 139.
8. See, for example: (a) Bauer, K.; Garbe, D.; Surburg, H. In Common Fragrance and Flavor Materials; Wiley-VCH: Weinheim, 2001.
9. (b) Ash, M.; Ash, I. In Handbook of Flavors and Fragrances; Synapse Information Resources, Inc: New York, 2006.
10. For recent reviews, accounts, and highlights dealing with the synthesis of furans, see: (a) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
11. (b) Keay, B. A. Chem. Soc. Rev. 1999, 28, 209.
12. (c) Jeevanandam, A.; Ghule, A.; Ling, Y.-C. Curr. Org. Chem. 2002, 6, 841.
13. (d) Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850.
14. (e) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076.
15. (f) D'Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095.
16. (g) Patil, N. T.; Yamamoto, Y. ARKIVOC 2007, (x), 121.
17. (h) Balme, G.; Bouyssi, D.; Monteiro, N. Heterocycles 2007, 73, 87.
18. Isomerization of allylic alcohols into carbonyl compounds: (a) Cadierno, V.; García-Garrido, S. E.; Gimeno, J. Chem. Commun. 2004, 232.
19. (b) Cadierno, V.; Crochet, P.; García-Garrido, S. E.; Gimeno, J. Dalton Trans. 2004, 3635.
20. (c) Crochet, P.; Díez, J.; Fernández-Zúmel, M. A.; Gimeno, J. Adv. Synth. Catal. 2006, 348, 93.
21. (d) Crochet, P.; Fernández-Zúmel, M. A.; Gimeno, J.; Scheele, M. Organometallics 2006, 25, 4846.
22. (e) Cadierno, V.; García-Garrido, S. E.; Gimeno, J.; Varela-Álvarez, A.; Sordo, J. A. J. Am. Chem. Soc. 2006, 128, 1360.
23. Reduction of allylic alcohols into saturated alcohols; (f) Cadierno, V.; Francos, J.; Gimeno, J.; Nebra, N. Chem. Commun. 2007, 2536.
24. Cycloisomerization of (Z)-enynols into furans: (g) Díaz- Álvarez, A. E.; Crochet, P.; Zablocka, M.; Duhayon, C.; Cadierno, V.; Gimeno, J.; Majoral, J. P. Adv. Synth. Catal. 2006, 348, 1671.
25. (h) Albers, J.; Cadierno, V.; Crochet, P.; García-Garrido, S. E.; Gimeno, J. J. Organomet. Chem. 2007, 692, 5234.
26. Intermolecular [2 + 2 + 2] alkyne cyclotrimerizations: (i) Cadierno, V.; García-Garrido, S. E.; Gimeno, J. J. Am. Chem. Soc. 2006, 128, 15094.
27. Meyer-Schuster and Rupe isomerizations of propargylic alcohols: (j) Cadierno, V.; Díez, J.; García-Garrido, S. E.; Gimeno, J. Chem. Commun. 2004, 2716.
28. (k) Cadierno, V.; García-Garrido, S. E.; Gimeno, J. Adv. Synth. Catal. 2006, 348, 101.
29. (l) Cadierno, V.; Díez, J.; García-Garrido, S. E.; Gimeno, J.; Nebra, N. Adv. Synth. Catal. 2006, 348, 2125.
30. Selective deprotection of N-allylic amines, amides, and lactams: (m) Cadierno, V.; García-Garrido, S. E.; Gimeno, J.; Nebra, N. Chem. Commun. 2005, 4086.
31. (n) Cadierno, V.; Gimeno, J.; Nebra, N. Chem. Eur. J. 2007, 13, 6590.
32. For reviews and books highlighting the burgeoning role of ruthenium catalysts in organic synthesis, see: (a) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507.
33. (b) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
34. (c) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev 2001, 101, 2067.
35. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
36. (e) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
37. (f) Ruthenium in Organic Synthesis; Murahashi, S.-I. Ed.; Wiley-VCH; Weinheim, 2004.
38. (g) Ruthenium Catalysts and Fine Chemistry; Bruneau, C., ; Dixneuf, P. H. Eds.; Springer: Berlin, 2004.
39. (h) Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630.
40. (i) Bruneau, C.; Dérien, S.; Dixneuf, P. H. Top. Organomet. Chem. 2006, 19, 295.
41. (j) Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176.
42. (k) Gimeno, J. Ruthenium Catalyzed Processes. Curr. Org. Chem. 2006, 10 (2), 113-225. (a thematic issue devoted to this topic)
43. Cadierno, V.; Gimeno, J.; Nebra, N. Adv. Synth. Catal. 2007, 349, 382.
44. We note that when a primary amine is introduced in the reaction media pyrroles instead of furans are selectively formed: (a) Cadierno, V.; Gimeno, J.; Nebra, N. Chem. Eur. J. 2007, 13, 9973.
45. Brønsted acid catalyzed propargylations of several organic substrates, including 1,3-dicarbonyl compounds, with alkynols have been reported: (a) Sanz, R.; Martínez, A.; Álvarez-Gutiérrez; J. M.; Rodríguez, F. Eur. J. Org. Chem. 2006, 1383.
46. (b) Sanz, R.; Miguel, D.; Martínez, A.; Álvarez- Gutiérrez, J. M.; Rodríguez, F. Org. Lett. 2007, 9, 727.
47. (c) Sanz, R.; Martínez, A.; Miguel, D.; Álvarez- Gutiérrez, J. M.; Rodríguez, F. Synthesis 2007, 3252.
48. (d) Yadav, J. S.; Reddy, B. V. S.; Rao, T. S.; Krishna, B. B. M.; Kumar, G. G. K. S. N. Chem. Lett. 2007, 36, 1472. In these works only 5 mol % of the acid is required to promote efficiently the propargylation process. In our case the use of larger quantities of TFA (50 mol %) is imperative in order to avoid the Meyer-Schuster isomerization of the propargylic alcohol catalyzed by the ruthenium complex 1. See refs 4k and 41.
49. In our previous work involving acyclic 1,3-dicarbonyl compounds (ref 6), the catalytic reactions were performed under "solvent-free" conditions, employing the 1,3-dicarbonyl compound (10 equiv with respect to the alkynol) itself as solvent. In order to avoid the waste of expensive reagents, we decided to reduce the quantity of the 1,3-diketone (1 equiv per equivalent of the alkynol), dissolving all the components of the catalytic reaction in the minimum amount of tetrahydrofuran.
50. See, for example: (a) Donnelly, D. M. X.; Boland, G. M. Nat. Prod. Rep. 1998, 241.
51. (b) Misky, M.; Jakupovic, J. Phytochemistry 1990, 29, 1995.
52. (c) Schuster, N.; Christiansen, C.; Jakupovic, J.; Mungai, M. Phytochemistry 1993, 34, 1179.
53. (d) Grese, T.; Pennington, L. D.; Sluka, J. P.; Adrian, M. D.; Cole, H. W.; Fuson, T. R.; Magee, D. E.; Phillips, D. L.; Rowley, E. R.; Shetler, P. K.; Short, L. L.; Venugopalan, M.; Yang, N. N.; Sato, M.; Glasebrook, A. L.; Bryant, H. U. J. Med. Chem. 1998, 41, 1272.
54. (e) Wang, X.; Bastow, K. F.; Sun, C.; Lin, Y.; Yu, H.; Don, M.; Wu, T.; Nakamura, S.; Lee, K. J. Med. Chem. 2004, 47, 5816.
55. (f) Zhao, L.; Brinton, R. D. J. Med. Chem. 2005, 48, 3463.
56. 3 has recently been reported: Huang, W.; Wang, J.; Shen, Q.; Zhou, X. Tetrahedron 2007, 63, 11636.
57. We note that such a reaction pathway is proposed in the closely related metal-catalyzed cyclizations of (Z)-enynols into furans. See, for example: (a) Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089.
58. (b) Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687.
59. No cyclizative C-C coupling reactions between alkynols and 1,3-cyclohexanediones have been reported. See, for example: (a) Gabbutt, C. D.; Hepworth, J. D.; Heron, B. M.; Partington, S. M.; Thomas, D. A. Dyes Pigm. 2001, 49, 65.
60. (b) Nakatsuji, S.; Yahiro, T.; Nakashima, K.; Akiyama, S.; Nakazumi, H. Bull. Chem. Soc. Jpn. 1991, 64, 1641.
61. Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Org. Chem. 2004, 69, 3408.
62. Transformation of terminal propargylic alcohols into allenylidene ligands in the coordination sphere of transition metals is a well-known process. For reviews on this topic, see: (a) Bruce, M. I. Chem. Rev. 1998, 98, 2797.
63. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J. Eur. J. Inorg. Chem. 2001, 571.
64. (d) King, R. B. Vinylidene, Allenylidene and Metallacumuiene Complexes. Coord. Chem. Rev. 2004, 248 (15-16), 1531-1703.
65. +: (a) Bustelo, E.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. Organometallics 2007, 26, 4300.