Three-component Barbier allylation-Friedel-crafts alkylation promoted by BuPyCl/SnCl2·2H2O: Application to the synthesis of 4-(substituted phenyl)chromans

Chinese Journal of Chemistry

Volumn 25, Issue 9, 2007, Pages 1312-1322

  Zhao, Xian Liang ^a   Liu, Li ^a   Chen, Yong Jun ^a   Wang, Dong ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

4 arylchromane; Barbier allylation; Friedel crafts alkylation; Ionic liquid; Three component reaction

Indexed keywords

EID: 34548601660     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200790244     Document Type: Article

References (60)

1. (a) Browers, W. S.; Ohta, T.; Cleere, J. S.; Marsella, P. A. Science 1976, 193, 542.
2. (b) Ellis, G. P.; Lockhart, I. M. Chromans and Tocopherols Wiley-Interscience, New York, 1981.
3. (c) Burton, G. W.; Doba, T.; Gabe, E.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053.
4. (d) De Cree, J.; Geukens, H.; Leempoels, J.; Verhaegen, H. Drug Dev. Res. 1986, 8, 109.
5. (e) Cichewicz, R. H.; Kenyon, V. A.; Whitman, S.; Morales, N. M.; Arguello, J. F.; Holman, T. R.; Crews, P. J. Am. Chem. Soc. 2004, 126, 14910 and references cited therein.
6. (a) Ogundaini, A.; Farah, M.; Perera, P. J. Nat. Prod. 1996, 59, 587.
7. (b) Hajela, K.; Pandey, J.; Dwivedy, A.; Dhar, J. D.; Sarkhel, S.; Maulik, P. R.; Velumurugan, D. Bioorg. Med. Chem. 1999, 7, 2083.
8. (c) Quaglia, W.; Pigini, M.; Piergentili, A.; Giannella, M.; Gentilli, F.; Marrucci, G.; Carrieri, A.; Carotti, A.; Pogges, E.; Leonardi, A.; Melchiorre, C. J. Med. Chem. 2002, 45, 1633.
9. (d) Sawadjoon, S.; Kittikara, K.; Vichai, V.; Tanticharoen, M.; Thebtaranonth, Y. J. Org. Chem. 2002, 67, 5470.
10. (e) Deng, J. Z.; Starck, S. R.; Li, S.; Hecht, S. M. J. Nat. Prod. 2005, 68, 1625.
11. (f) Maloney, D. J.; Starck, S. R.; Gao, Z.; Hechit, S. M. J. Am. Chem. Soc. 2005, 127, 4140-4141.
12. (a) Baterman, G.; Brown, B. R.; Campbell, J. B.; Cotton, A. C.; Johnson, P.; Mulqueen, P.; O'Nell, D.; Shaw, M. R.; Smith, R. A.; Troke, J. A. J. Chem. Soc., Perkin Trans. 1 1983, 2903.
13. (b) Adegoke, E. A.; Emokpae, T. A.; Ephraim-Bassey, H.; POyelola, C. A. J. Heterocycl. Chem. 1987, 24, 1705.
14. For example, see: (a) Larock, R. C.; Yang, H.; Pace, P. Tetrahedron Lett. 1998, 39, 237.
15. (b) Trost, B. M.; Asakawa, N. Synthesis 1999, 1491.
16. (c) Nicolaou, K. C.; Pfefferkorn, J. A.; Barluenga, S.; Mitchell, H. J.; Roecker, A. J.; Cao, G. Q. J. Am. Chem. Soc. 2000, 122, 9968.
17. (d) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. J. Am. Chem. Soc 2004, 126, 3416.
18. (e) Merchaet, A.; Delbeke, P.; Daloze, D.; Dive, G. Tetrahedron Lett. 2004, 45, 4697.
19. (f) Trost, B. M.; Shen, H. C.; Surivet, J. P. J. Am. Chem. Soc. 2004, 126, 12565.
20. (g) Vyvyan, J. R.; Oaksmith, J. M.,; Parks, B. W.; Peterson, E. M. Tetrahedron Lett. 2005, 46, 2457.
21. (a) Shiina, I.; Suzuki, M. Tetrahedron Lett. 2002, 43, 6391.
22. (b) Mertins, K.; Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 238, and references cited therein.
23. (a) Malkov, A. V.; Davis, S. L.; Baxendale, I. R.; Mitchell, W. L.; Kocovsky, P. J. Org. Chem. 1999, 64 2751.
24. (b) Malkov, A. V.; Spoor, P.; Vinader, V.; Kocovsky, P. J. Org. Chem. 1999, 64, 5308.
25. (c) Song, H. S.; Lee, H. J.; Kim, H. R.; Ryu, E. K.; Kim, J. N. Synth. Commun. 1999, 29, 3303.
26. (d) Chen, Y. J.; Ge, C.-S.; Wang, D. Synlett 2000, 1429.
27. (e) Gong, Y.; Kato, K.; Kimoto, H. Bull. Chem. Soc. Jpn. 2001, 74, 377.
28. (f) Chen, Y. J.; Lei, F.; Wang, D. Tetrahedron 2003, 59, 7609.
29. (g) For review on Barbier reaction, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
30. (a) Shiina, I.; Suzuki, M.; Yokoyama, K. Tetrahedron Lett. 2002, 43, 6395.
31. (b) Shiina, I.; Suzuki, M.; Yokoyama, K. Tetrahedron Lett. 2004, 45, 965.
32. Roy, U. K.; Jana, P. K.; Roy, S. Tetrahedron Lett. 2007, 48, 1183.
33. (a) Zhu, J.; Bienayme, H. Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
34. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
35. Zhao, X. L.; Liu, L.; Chen, Y. J.; Wang, D. Tetrahedron 2006, 62, 7113
36. For examples, see: (a) Imai, T.; Nishida, S. Chem. Commun. 1994, 277.
37. (b) Tan, X.-H.; Shen, B.; Deng, W.; Zhao, H.; Liu, L.; Guo, Q.-X. Org. Lett. 2003, 5, 1833.
38. (c) Jang, T. S.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Synthesis 2003, 775.
39. (d) Masuyama, Y.; Kaneko, Y.; Kurusu, Y. Tetrahedron Lett. 2004, 45, 8969-8971.
40. (a) Masuyama, Y.; Kishida, M.; Kurusu, Y. Tetrahedron Lett. 1996, 37, 7103.
41. (b) Masuyama, Y.; Ito, A.; Kurusu, Y. Chem. Commun. 1998, 315.
42. (c) Masuyama, Y.; Ito, T.; Tachi, K.; Ito, A.; Kurusu, Y, Chem. Commun. 1999, 1261.
43. (d) Ito, A.; Kishida, M.; Kurusu, Y.; Masuyama, Y. J. Org. Chem. 2000, 65, 494.
44. (a) Parshall, G. W. J. Am. Chem. Soc. 1972, 94, 8716.
45. (b) Wasserscheid, P.; Waffenschmidt, H. J. Mol. Catal. A: Chem. 2000, 164, 61.
46. Sato, K.; Yoshimura, T.; Shindo, M.; Shishido, K. J. Org. Chem. 2001, 66, 309.
47. Fousteris, M.; Chevrin, C.; Bras, J. L.; Muzart, J. Green Chem. 2006, 8, 522.
48. For examples of suitable catalysts, see: (a) TfOH: Coulombel, L.; Dunach, E. Green Chem. 2004, 6, 499.
49. 3: Bolzoni, L.; Casiraghi, G.; Casnati, G.; Sartori, G. Angew. Chem., Int. Ed. Engl. 1978, 17, 684.
50. 2: Talyor, J. G.; Whittall, N. Hii, K. K. (Mim) Chem. Commun. 2005, 5103.
51. 4: Coulombel, Favier, I.; Dunach, E. Chem. Commun. 2005, 2286.
52. (e) Rh(I): Bienayme, H.; Ancel, J. E.; Meilland, P.; Simonato, J.-P. Tetrahedron Lett. 2000, 41, 3339.
53. (f) Pt(II): Qian, H.; Han, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536.
54. (g) Ru(II): Oe, Y.; Ohta, T.; Ito, Y. Chem. Commun. 2004, 1620.
55. (h) Au(I): Yang, C.-G.; He, Ch. J. Am. Chem. Soc. 2005, 127, 6966.
56. (i) Pd(II): Gligorich, K. M.; Schultz, M. J.; Sigman, M. S. J. Am. Chem. Soc. 2006, 128, 2794.
57. (j) NBS: Talluri, S. K.; Sudalai, A. Org. Lett. 2005, 7, 855.
58. Nguyen, R. V.; Yao, X.; Li, C. J. Org. Lett. 2006, 8, 2397
59. Youn, S. W.; Eom, J. I. J. Org. Chem. 2006, 71, 6705
60. Rosenfeld, D. C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J. F. Org. Lett. 2006, 8, 4179.