Iron-catalyzed cascade arene-aldehyde addition/cyclizations for the highly efficient synthesis of xanthenes and its analogous: Observation of a C-C bond cleavage in indole-based triarylmethanes

Journal of Organic Chemistry

Volumn 74, Issue 17, 2009, Pages 6797-6801

  Li, Hongfeng ^a,b   Yang, Jingyu ^a,b   Liu, Yuanhong ^a   Li, Yanzhong ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BONDS; CATALYZED REACTIONS; CHEMICAL EQUATIONS; DOMINO PROCESS; EFFICIENT SYNTHESIS; ELECTRON-RICH ARENES; HIGH SELECTIVITY; MECHANISTIC STUDIES; MILD REACTION CONDITIONS; ONE-POT PROCEDURES; STARTING MATERIALS;

ALDEHYDES; CHEMICAL REACTIONS; IRON COMPOUNDS;

CHEMICAL BONDS;

ALDEHYDE; CARBON; FERRIC ION; INDOLE DERIVATIVE; METHANE; POLYCYCLIC AROMATIC HYDROCARBON; XANTHENE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; DISSOCIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 69549120370     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9012354     Document Type: Article

References (78)

1. For reviews, see: (a) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217.
2. (b) Díaz, D. D.; Miranda, P. O.; Padrón, J. I.; Martín, V. S. Curr. Org. Chem. 2006, 10, 457.
3. For selected papers, see: (a) Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K.-Y. Angew. Chem. 2000, 112, 3582 ;
4. Angew. Chem., Int. Ed. 2000, 39, 3440 .
5. (b) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem. 2004, 116, 560 ;
6. Angew. Chem., Int. Ed. 2004, 43, 550 .
7. (c) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692.
8. (d) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681.
9. (e) Jia, C. G.; Lu, W. T.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252.
10. (f) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
11. (g) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
12. (h) Pastine, S. J.; Sames, D. Org. Lett. 2003, 5, 4053.
13. (i) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055.
14. (j) Sezen, B.; Sames, D. Org. Lett. 2003, 5, 3607.
15. (a) Nair, V.; Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 7, 5857.
16. (b) Esquivias, J.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 629.
17. (c) Alonso, I.; Esquivias, J.; Gómez-Arrayás, R.; Carretero, J. C. J. Org. Chem. 2008, 73, 6401.
18. (d) Podder, S.; Choudhury, J.; Roy, U. K.; Roy, S. J. Org. Chem. 2007, 72, 3100.
19. (e) Schaarschmidt, A.; Hermann, L.; Szemzo, B. Ber. 1925, 58, 1914.
20. (f) Ji, S.-J.; Zhou, M.-F.; Gu, D.-G.; Jiang, Z.-Q.; Loh, T.-P. Eur. J. Org. Chem. 2004, 1584.
21. (g) Li, Z.; Duan, Z.; Kang, J.; Wang, H.; Yu, L.; Wu, Y. Tetrahedron 2008, 64, 1924.
22. (h) Kodomari, M.; Nagamatsu, M.; Akaike, M.; Aoyama, T. Tetrahedron Lett. 2008, 49, 2537.
23. (i) Temelli, B.; Unaleroglu, C. Tetrahedron Lett. 2005, 46, 7941.
24. (j) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751.
25. (k) Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv. Synth. Catal. 2003, 345, 557.
26. (l) Yadav, J. S.; Reddy, B. V. S.; Sunitha, S. Adv. Synth. Catal. 2003, 345, 349.
27. (m) Yadav, J. S.; Reddy, B. V. S.; Murthy, C. V. S. R.; Kumar, G. M.; Madan, C. Synlett 2001, 783.
28. (n) Lee, H. J.; Seong, M. R.; Song, H. N.; Kim, J. N. Bull. Korean Chem. Soc. 1999, 20, 267.
29. (o) Alvaro, M.; García, H.; Sanjuán, A.; Esplá, M Appl. Catal., A 1998, 175, 105.
30. (a) Das, S. K.; Shagufta, P. G. Tetrahedron Lett. 2005, 46, 3097.
31. (b) Burmester, A.; Stegmann, H. B. Synthesis 1981, 125.
32. (c) Pratt, E. F.; Green, L. Q. J. Am. Chem. Soc. 1953, 75, 275.
33. (d) Katrizky, A. R.; Toader, D. J. Org. Chem. 1997, 62, 4137.
34. (e) Katrizky, A. R.; Gupta, V.; Garot, C.; Stevens, C. V.; Gordeev, M. F. Heterocycles 1994, 38.
35. (f) Katrizky, A. R.; Lan, X.; Lam, J. M. Chem. Ber. 1991, 124, 1809.
36. (a) Li, G.; Zhou, S.; Su, G.; Liu, Y.; Wang, P. G. J. Org. Chem. 2007, 72, 9830.
37. (b) Liu, Y.; Zhou, S.; Li, G.; Yan, B.; Guo, S.; Zhou, Y.; Zhang, H.; Wang, P. G. Adv. Synth. Catal. 2008, 350, 797.
38. (c) Li, G.; Wang, E.; Chen, H.; Li, H.; Liu, Y.; Wang, P. G. Tetrahedron 2008, 64, 9033.
39. (d) Guo, S.; Liu, Y. Org. Biomol. Chem. 2008, 6, 2064.
40. (a) Bénisvy, L.; Chottard, J. -C.; Li, J. M. Y. Eur. J. Inorg. Chem. 2005, 999.
41. (b) Dhakshinamoorthy, A.; Pitchumani, K. Tetrahedron 2006, 62, 9911.
42. (c) Nakazawa, H.; Itazaki, M.; Kamata, K.; Ueda, K. Chem. Asian J. 2007, 2, 882.
43. (d) Paine, T. K.; England, J.; Que, L. Jr. Chem.;Eur. J. 2007, 13, 6073.
44. (a) Yeager, G. W.; Schissel, D. N. Synthesis 1995, 28.
45. (b) Wang, J. Q.; Harvey, R. G. Tetrahedron 2002, 58, 5927.
46. For iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates with electron-rich arenes, see: Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 3913.
47. CCDC-727316 (compound 2c) and CCDC-727317 (compound 2k) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
48. (a) Rys, P.; Zollinger, H. In Fundamentals of the Chemistry and Application of Dyes; Wiley-Interscience: NewYork, 1972.
49. (b) Muthyala, R. In Chemistry and Applications of Leuco Dyes; Katrizky, A. R., Sabongi, G. J., Eds.; Plenum: New York, 1997.
50. (a) Aldag, R. Photochromism Based on Dissociation Processes. In Photochromism: Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: London, UK, 1990.
51. (b) Sanguinet, L.; Twieg, R. J.; Wiggers, G.; Mao, G.; Singer, K. D.; Petschek, R. G. Tetrahedron Lett. 2005, 46, 5121.
52. (c) Noack, A.; Hartmann, H. Chem. Lett. 2002, 644.
53. (a) Sirkeeioglu, O.; Talinli, N.; Akar, A. J. Chem. Res., Synop. 1995, 502.
54. (b) Ahmad, M.; King, T. A.; Ko, D. K.; Cha, B. H.; Lee, J. J. Phys. D: Appl. Phys. 2002, 35, 1473.
55. (a) Knight, C. G.; Stephens, T. Biochem. J. 1989, 258, 683.
56. (b) Li, J.; Yao, S. Q. Org. Lett. 2009, 11, 405.
57. Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Parkes, K. E. B.; Thomas, G. J. PCT Int. Appl. WO9706178, 1997;
58. Chem. Abstr 1997, 126, 212377 .
59. Hideo, T. Jpn. Kokai Tokkyo Koho JP 56005480, 1981; Chem. Abstr. 1981, 95, 80922.
60. Poupelin, J. P.; Saint-Rut, G.; Foussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lacroix, R. Eur. J. Med. Chem. 1978, 13, 67.
61. (a) Wang, J.-Q.;Harvey, R. G. Tetrahedron 2002, 58, 5927.
62. (b) Yang, Y.; Escobedo, J. O.; Wong, A.; Schowalter, C. M.; Touchy, M. C.; Jiao, L.; Crowe, W. E.; Fronczek, F. R.; Strongin, R. M. J. Org. Chem. 2005, 70, 6907.
63. (c) Su, W.; Yang, D.; Jin, C.; Zhang, B. Tetrahedron Lett. 2008, 49, 3391.
64. (d) Caruso, A. J.; Lee, J. L. J. Org. Chem. 1997, 62, 1058.
65. (e) Agbaria, K.; Biali, S. E. J. Org. Chem. 2001, 66, 5482.
66. (f) Zhao, J.; Larock, R. C. J. Org. Chem. 2007, 72, 583.
67. (g) Okuma, K.; Nojima, A.; Matsunaga, N.; Shioji, K. Org. Lett. 2009, 11, 169.
68. (a) Roberts, R. M.; El-Khawaga, A. M.; Sweeney, K. M.; El-Zohry, M. F. J. Org. Chem. 1987, 52, 1591.
69. (b) Alvara, M.; García, H.; Sanjuán, A.; Esplá, M. Appl. Catal. A 1998, 175, 105.
70. (c) De Vries, T. S.; Vedejs, E. Organometallics 2007, 26, 3079.
71. (a) Griepentrog, H. Ber. Dtsch. Chem. Ges. 1886, 19, 1876.
72. (b) Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081.
73. (c) Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 11211.
74. For the effect of additives, see refs 3g and 3h.
75. We have reported that benzyl acetates are better substrates compared with that of benzyl alcohols in various acid-catalyzed Friedel-Crafts reactions, see refs 5a-c.
76. 2O; however, no desired product was observed, and most of the starting material remained.
77. 1H NMR spectra, compounds 2n and 2o have diastereotopic methyl groups, while compound 11 appears not to, and compound 9 has broad methyls.
78. 2O, we did not observe the intermediates of triarylmethane.