A general method for the synthesis of 3,5-diarylcyclopentenones via Friedel-Crafts acylation of vinyl chlorides

Journal of Organic Chemistry

Volumn 74, Issue 14, 2009, Pages 5100-5103

  Xu, Yingju ^a   McLaughlin, Mark ^a   Chen, Cheng Yi ^a   Reamer, Robert A ^a   Dormer, Peter G ^a   Davies, Ian W ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; ARYLACETIC ACIDS; CHEMICAL EQUATIONS; CROSS COUPLING REACTIONS; CROSS-COUPLING; CYCLOPENTENONES; FRIEDEL-CRAFTS; FRIEDEL-CRAFTS ACYLATION; GENERAL APPROACH; GENERAL METHOD; VINYL CHLORIDES;

ACIDS; CHEMICAL BONDS; CHLORINE COMPOUNDS; CYCLIZATION; ESTERS; HYDROCARBONS; REACTION KINETICS;

PALLADIUM;

ALUMINUM CHLORIDE; CYCLOPENTENONE DERIVATIVE; PALLADIUM; VINYL CHLORIDE;

ACYLATION; ALKYLATION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; FRIEDEL CRAFTS REACTION; SUZUKI REACTION; SYNTHESIS;

ACYLATION; CYCLIZATION; MOLECULAR STRUCTURE; PENTANONES; VINYL CHLORIDE;

EID: 67650398306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900696k     Document Type: Article

References (60)

1. Friedel, C.; Crafts, J. M. Compt. Rend. 1877, 84, 1392 and 1450.
2. For reviews see: (a) Price, C. C. Org. React. 1946, 3, 1.
3. (b) Groves, J. K. Chem. Soc. Rev. 1972, 1, 73.
4. (c) Heaney, H. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 2, p 733.
5. (d) Gore, P. H. Chem. Ind. 1974, 18, 727.
6. (e) Olah, G. A. Friedel-Crafts Chemistry; Wiley: New York, 1973.
7. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 10, 533.
8. For new catalysts see: (g) Kangani, C. O.; Billy, W. D. Org. Lett. 2008, 10, 2645.
9. (h) Sartori, G.; Maggi, R. Chem. Rev. 2006, 106, 1077.
10. For enantioselective F-C reactions see: (i) Majer, J.; Kwiatkowski, P.; Jurczak, J. Org. Lett. 2008, 10, 2955.
11. (j) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
12. (k) Jørgensen, K. A. Synthesis 2003, 1117.
13. (l) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550.
14. (a) Franck-Neumann, M.; Miesch-Gross, L.; Nass, O. Tetrahedron Lett. 1996, 37, 8763.
15. (b) Waser, M.; Falk, H. Monatsh. Chem. 2005, 136, 609.
16. For reviews see: (c) Heaney, H. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 2, p 753.
17. (d) Sethna, S Friedel-Crafts and Related Reactions, Olah, G. A., Ed.; Interscience: New York, 1964; Vol. 3, p 911.
18. (e) Gore, P. H. Chem. Rev. 1955, 55, 229-281.
19. (a) Drouin, J.; Conia, J. M. Synth. Commun. 1982, 12, 81.
20. (b) Drouin, J.; Leyendecker, F.; Conia, J. M. Tetrahedron 1980, 36, 1203.
21. (c) Fraser, F. A.; Proctor, G. R.; Redpath, J. J. Chem. Soc., Perkin Trans. I 1992, 445.
22. For other utility of chloro olefin see: (d) Lansbury, P. T. Acc. Chem. Res. 1972, 5, 311.
23. For selected synthesis of substituted 2-cyclopentenone see: (a) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
24. (b) Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442.
25. (c) Arcadi, A.; Marinelli, F.; Pini, E.; Rossi, E. Tetrahedron Lett. 1996, 37, 3387.
26. (d) Prempree, P.; Siwapinyoyos, T.; Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron Lett. 1980, 21, 1169.
27. (e) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5881.
28. Through [4+1] annulation see: (f) Moser, W. H.; Feltes, L. A.; Sun, L.; Giese, M. W.; Farrell, R. W. J. Org. Chem. 2006, 71, 6542.
29. (g) Davie, C. P.; Danheiser, R. L. Angew. Chem., Int. Ed. 2005, 44, 5867.
30. (h) Kurahashi, T.; Wu, Y.-T.; Meindl, K.; Rühl, S.; Meijere, A. Synlett. 2005, 5, 805.
31. For zirconium-catalyzed see: (i) Takahashi, T.; Huo, S.; Hara, R.; Noguchi, Y.; Nakajima, K; Sun, W. J. Am. Chem. Soc. 1999, 121, 1094.
32. (j) Xi, Z.; Fan, H.; Mito, S.; Takahashi, T. J. Organomet. Chem. 2003, 682, 108.
33. (k) Yuki, T.; Hashimoto, M.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1993, 58, 4497.
34. For Pd-catalyzed see: (l) Tsukada, N.; Sugawara, S.; Okuzawa, T.; Inoue, Y. Synthesis 2006, 18, 3003.
35. For rhodium(I)-catalyzed see: (m) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307.
36. (n) Matsuda, I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241.
37. (o) Matsuda, I.; Fukuta, Y.; Tsuchihashi, T.; Nagashima, H.; Itoh, K. Organometallics 1997, 16, 4327.
38. Through iron complex see: (p) Stokes, H. L.; Ni, L. M.; Belot, J. A.; Welker, M. E. J. Organomet. Chem. 1995, 487, 95.
39. (q) Ni, L.; Belot, J. A.; Welker, M. E. Tetraohedron Lett. 1992, 33, 177.
40. For Cobalt-catalyzed syntheses see: (r) Krafft, M. E. J. Am. Chem. Soc. 1988, 110, 968.
41. (s) Rao, M. L. N.; Periasamy, M. Organomettallics 1996, 15, 442.
42. (t) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans 1 1973, 977.
43. (a) Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 2892.
44. (b) Chae, J.; Yun, J.; Buchwald, S. L. Org. Lett. 2004, 6, 4809.
45. (c) Yun, J.; Buchwald, S. L. Org. Lett. 2001, 3, 1129.
46. (a) May, T. L.; Brown, M. K.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2008, 47, 7358.
47. (b) Vuagnoux-d'Augustin, M.; Kehrli, S.; Alexakis, A. Synlett 2007, 13, 2057.
48. (c) Zezschwitz, P. Synthesis 2008, 12, 1809.
49. (a) Chen, C.; Frey, L. F.; Shultz, S.; Wallace, D. J.; Marcantonio, K.; Payack, J. F.; Vazquez, E.; Springfield, S. A.; Zhou, G.; Liu, P.; Kieczykowski, G. R.; Chen, A. M.; Phenix, B. D.; Singh, U.; Strine, J.; Izzo, B.; Krska, S. W. Org. Proc. Res. Dev. 2007, 11, 616.
50. (b) Rosen, J. D.; Nelson, T. D.; Huffman, M. A.; McNamara, J. M. Tetrahedron Lett. 2003, 44, 365.
51. (c) Chen, C.; Dagneau, P.; Grabowski, E. J. J.; Oballa, R.; O'Shea, P.; Prasit, P.; Robichaud, J.; Tillyer, R.; Wang, X. J. Org. Chem. 2003, 68, 2633.
52. Direct alkylation on free acids with nBuLi (conditions B) gave lower isolated yield than conditions A.
53. (a) Murray, A.; Hansen, J. B.; Christensen, B. V. Tetrahedron 2001, 57, 7383.
54. For Pd-mediated coupling of 3-chlorocyclopentenone derivative (Stille coupling) see: (b) Araki, K.; Saito, K.; Arimoto, H.; Uemura, D. Angew. Chem., Int. Ed. 2004, 43, 81.
55. For selective examples of cross-coupling reactions between 3-bromo or 3-iodo cyclopentenones and aryl or vinyl boronic acids see: (c) Marson, C. M.; Farrand, L. D.; Dunmur, D. A. Tetrahedron 2003, 59, 4377.
56. (d) Genêt, J. P.; Linquist, A.; Blart, E.; Mouriès, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443.
57. (e) Conchon, E.; Anizon, F.; Aboab, B.; Prudhomme, M. J. Med. Chem. 2007, 50, 4669.
58. (f) Okamoto, K.; Akiyama, R.; Kobayashi, S. Org. Lett. 2004, 6, 1987.
59. 2, in dioxane or dioxane/water at 70°C. X-phos and 2-dicyclohexyldiphenylphosphine gave faster reactions and higher assay yields, where X-phos gave highest assay yield in dioxane.
60. The solvents used in these experiments were not degassed.