A new, expeditious entry to the benzophenanthrofuran framework by a Pd-catalyzed C- And O-arylation/PIFA-M ediated oxidative coupling sequence

European Journal of Organic Chemistry

Volumn , Issue 12, 2005, Pages 2481-2490

  Churruca, Fátima ^a   Sanmartin, Raul ^a   Tellitu, Imanol ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Fused ring systems; Heterogeneous catalysis; Oxidative coupling; Oxygen heterocycles; Palladium

Indexed keywords

EID: 20744456158     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400856     Document Type: Article

References (88)

1. Resveratrol dimers anigopreissin A and gnetuhainins B and F are isolated from the roots of Anigozanthos preissi, Musu cavendishii and the lianas of Gnetum hainanense, respectively. The tetrameric compounds vitisifurans A and B and amurensins L and M are isolated from the roots and corks of Vitis vinifera and Vitis amurensis, respectively. For their isolation, strong anti-inflammatory and anti-histaminic properties, and their use as traditional antihepatotoxic drugs in Oriental medicine, see: a) Y. Oshima, A. Kamijou, H. Moritani, K.-I. Namao, Y Ohizumi, J. Org. Chem. 1993, 58, 850-853;
2. b) J. Ito, Y. Takaya, Y. Oshima, M. Niwa, Tetrahedron 1999, 55, 2529-2544;
3. c) K.-S. Huang, M. Lin, G.-F. Cheng, Phytochemistry 2001, 58, 357-362 and references cited therein;
4. d) B. Scheneider, Phytochemistry 2003, 64, 459-462;
5. see also: e) T. S. Wu, M. Y. Hsu, A. G. Damu, P. C. Kuo, C. R. Su, C. Y. Li, H. D. Sun, Heterocycles 2003, 60, 397-404.
6. The employment of diarylbenzofurans as cyclooxygenase-2 (COX-2) inhibitors has been claimed for the treatment of inflammatory disorders. See, for example: a) H.-C. Huang, T. S. Chamberlain, K. Seibert, C. M. Koboldt, P. C. Isakson, D. B. Reitz, Bioorg. Med. Chem. Lett. 1995, 5, 2377-2380;
7. b) F. S. Caruso, (Algos Pharmaceutical Corp., USA) 2000, WO 20000525 (Chem. Abstr. 132:343345);
8. c) H. M. Elokdah, G. R. Mcfarlane, S. C. Mayer, D. L. Crandall, (Wyeth, John, and Brother Ltd., USA), 2003, WO 2003000671 (Chem. Abstr. 138:73168);
9. Diarylbenzofurans have been reported to show noteworthy activity against certain types of cancer, probably due to their ability to inhibit polymerisation of tubulin, see: d) B. L. Flynn, E. Hamel, M. K. Jung, J. Med. Chem. 2002, 45, 2670-2673;
10. for some technological applications of diarylbenzofurans, such as their use as organic electroluminescent devices, see: e) M. Funabashi, H. Kawamura, H. Azuma, C. Hosokawa (Idemitsu Kasan Co., Japan) 2000, JP 20000711 (Chem. Abstr. 133:96595).
11. The common methods involving the formation of one bond (single or double) of the heterocycle are i) arylation of 2-arylfuran precursors: a) W.-M. Dai, K. W. Lai, Tetrahedron Lett. 2002, 43, 9377-9380;
12. cyclodehydration of 2-aryloxy-1,2-diarylethanones: b) M. Jorgensen, F. C. Krebs, K. Bechgaard, J. Org. Chem. 2000, 65, 8783-8785;
13. McMurry coupling of o-acyloxybenzophenones: c) A. Fürstner, A. Hupperts, G. Seidel, Org. Synth. 1999, 76, 142-150;
14. intramolecular [2+2] cycloaddition of carbonyl and ketene moieties: d) W. T. Brady, Y. F. Giant, A. P. Marchand. A. H. Wu, J. Org. Chem. 1987, 52, 3457-3461;
15. photocyclisation of 2-benzyloxybenzophenones: e) G. R. Lappin, I S. Zannuci, J. Org. Chem. 1971, 36, 1808-1811;
16. treatment of 2′-alkoxybenzoins with HI,: f) R. E. Koenigkramer, H. Zimmer, J. Org. Chem. 1980, 45, 3994-3998;
17. photolysis of arylvinyl bromides and vinylbenzoquinones: g) C. Galli, P. Gentili, A. Guarnieri, S. Kobayashi, Z. Rappoport, J. Org. Chem. 1998, 63, 9292-9299;
18. h) H. Iwamoto, A. Takuwa, K. Hamada, R. Fujiwara, J. Chem. Soc., Perkin Trans. 1 1999, 575-581;
19. electrocyclisation of diaryl-α-acylcarbocationic species: i) M. Schmittel, A. Burghart, H. Werner, M. Laubender, R. Söllner, J. Org. Chem. 1999, 64, 3077-3085;
20. j) N. Yoshida, T. Ohwada, Synthesis 2001, 1487-1494,.
21. See also: k) M. A. Ashraf, M. A. Jones, N. E. Kelly, A. Mullaney, J. S. Snaith, I. Williams, Tetrahedron Lett. 2003, 44, 3151-3154.
22. The access to diarylbenzofurans has been reported by sequential formation of two or more bonds of the furan ring, using the following procedures: i) condensation between benzoins and phenols in acidic media: a) B. J. Morrison, O. C. Musgraves, Tetrahedron 2002, 58, 4225-4260;
23. intermolecular nucleophilic attack of phenols to diaryl cations: b) H. D. Choi, P. J. Seo, S.W. Son, J. Korean Chem. Soc. 2001, 45, 500-504;
24. 1,3-dipolar cycloadditions of o-substituted phenols and alkynes: c) S. Spyroudis, J. Org. Chem. 1986, 57, 3453-3456;
25. palladium-catalysed multi-component coupling of arylalkynes, haloarenes and o-halophenols, see ref. [2c]; v) tandem α-arylation/heterocyclisation of deoxybenzoins: d) V. R. Veeramaneni, M. Pal, K. R. Yeleswarapu, Tetrahedron 2003, 59, 3283-3290.
26. Y. Terao, T. Satoh, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1999, 72, 2345-2350; for a recent application, see also ref. [4d].
27. For the employment of phenanthro[9,10] heterocycles in the construction of calixarenes applicable to molecular recognition and/or catalysis, see: E. Botana, K. Nättinen, P. Prado, K. Rissanen, J. de Mendoza, Org. Lett. 2004, 6, 1091-1094.
28. F. C. Krebs, H. S. Spanggaard, J. Org. Chem. 2002, 67, 7185-7192 and references cited therein.
29. L. Bu, T. Sawada, H. Shosenji, K. Yoshida, S. Mataka, Dves Pigments 2003, 57, 181-195.
30. K. Z. Wang, L.-H. Gao, G.-Y. Bai, L.-P. Jin, Inorg. Chem. Commun. 2002, 5, 841-843.
31. E. N. Sidorenko, T. Y. Dutova (Optiva, USA), 2003, US 6583284 8 (Chem. Abstr. 139:69282).
32. W. Zhao, E. M. Carreira (Johnson & Johnson Vision Care, USA), 2003, WO 2003042195 (Chem. Abstr. 138:403077).
33. a) T. Tominaga, A. Makiyama, T. Kohama (Toray Industries, Japan), 2003, JP 2003059670 (Chem. Abstr. 138:212567);
34. b) T. Ishida, T. Shimamura, M. Nakatsuka (Mitsui Chemicals, Japan), 2002, JP 2002043061 (Chem. Abstr. 136:158603).
35. Their application to the manufacture of several electronic devices, such as diodes, transistors and wiring materials has been reported, see: a) S. Ogawa, K. Ogawa, N. Yoshimoto, Y. Hiroi, (Japan Science and technology Corp., Japan) 2002, JP2002265466 (Chem. Abstr. 137:247701); as a consequence of their planar structure, DNA intercalation of phenanthro[9,10] heterocycles has attracted much attention, closely related to the fact that interaction with DNA can be monitored by the change of fluorescence intensity,
36. see: b) S.-H. Yang, J.-J. Shie, J.-M. Fang, S. K. Nandy, H.-Y. Chang, S.-H. Lu, G. Wang, J. Org. Chem. 2002, 67, 5208-5215;
37. c) H. Zeytinoglu, E. Ergene, B. A. Tueylue, Drug. Chem. Toxicol. 2003, 26, 245-257;
38. finally, antibacterial and antifungal activity have been claimed in: d) A. A. Pechkin, M. M. El'chaninov, V. M. Stoyanov, Russ. J. Org. Chem. 2002, 38, 726-730;
39. e) M. Huesca, R. Alqawasmeh, A. H. Young, Y. Lee, (Lorus Therapeutics, Canada) 2004, WO 2004016086 (Chem. Abstr. 140:193035).
40. F. Churruca, R. SanMartin, M. Carril, I. Tellitu, E. Domínguez, Tetrahedron 2004, 60, 2393-2408.
41. In fact, triarylethanones of type 5 are currently being employed in our research group for the synthesis of several heterocyclic systems, such as diarylindoles. The corresponding results will be published in due course.
42. For a recent review, see: G. Lessene, K. S. Feldman, in Modern Arene Chemistry (Ed.: D. Astruc), Wiley VCH, Weinheim (Germany), 2002, pp. 479-538.
43. a) C. Amatore, E. Blart, J. P. Genêt, A. Jutand, S. Lemaire-Audoire, M. Savignac, J. Org. Chem. 1995, 60, 6829-6839;
44. b) D. E. Bergbreiter, B. L. Case, Y.-S. Liu, J. W. Caraway, Macro-molecules 1998, 31, 6053-6062.
45. For arylation reactions that imply formation of C-heteroatom bonds, see: a) M. R. Buchmeiser, K. Wurst, J. Am. Chem. Soc. 1999, 121, 11 101-11 107;
46. b) T. Hashizume, K. Yonehara, K. Ohe, S. Uemure, J. Org. Chem. 2000, 65, 5197-5201;
47. C. A. Parrish, S. L. Buchwald, J. Org. Chem. 2001, 66, 3820-3827;
48. M. R. Buchmeiser, T. Schareina, R. Kempe, K. Wurst, J. Organomet. Chem. 2001, 634, 34-46.
49. Bifunctional palladium and/or other metal catalysts are required. An elegant example can be found in: B. M. Choudary, N. S. Chowdary, S. Madhi, M. Kantam, J. Org. Chem. 2003, 68, 1736-1746.
50. The above-described isolation of intermediate triarylethanones 5a,b is in clear accordance with such a mechanistic proposal. For a more detailed discussion on this subject see ref. [5].
51. Among heterogeneous palladium catalysts, the use of polymersupported and polymer-incarcerated catalysts has gained much attention in the last few years. In fact, catalysis has become an obvious and important area of application for functionalised polymers, and is already established in fundamental synthetic protocols, such as hydrogenation, allylic alkylation or Suzuki and Heck coupling reactions. For some recent examples, see: a) K. Okamoto, R. Akiyama, S. Kobayashi, Org. Lett. 2004, 6, 1987-1990;
52. b) J. W. Byun, Y. S. Lee, Tetrahedron Lett. 2004, 45, 1837-1840;
53. A. Drelinkiewicza, A. Waksmundzka, W. Makowski, J. W. Sobczak, A. Krol, A. Zieba, Catal. Today 2004, 93, 143-146.
54. For a schematic view of these FibreCat™ catalysts, see ref. [14]. The FibreCat™ 1000 series is commercialized by Johnson Matthey Chemicals, Orchard Road, Royston, Herts, SG8 5HE, UK. Further information about FibreCat™ catalysts, including their practical application to Suzuki and Heck coupling reactions, can be found at http://www.chemicals.matthey.com.
55. a) F. Churruca, R. SanMartin, I. Tellitu, E. Domínguez, Tetrahedron Lett. 2003, 44, 5925-5929.
56. For other examples of such phenyl-aryl exchange, see: b) V. V. Grushin, Organometallics 2000, 19, 1888-1900;
57. c) M. Jayakannan, J. L. J. van Dongen, R. A. J. Janssen, Macromolecules 2001, 34, 5386-5393;
58. d) F. Y. Kwong, C. W. Lai, K. S. Chan, J. Am. Chem. Soc. 2001, 123, 8864-8865;
59. e) F. Y. Kwong, C. W. Lai, K. S. Chan, Tetrahedron Lett. 2002, 43, 3537-3539.
60. A. D. Whiting, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, Exeter, 1991, vol. 3, pp. 659-703.
61. a) Metal-Catalysed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, Germany, 1998;
62. b) H. Abe, S. Takeda, Y. Takeuchi, T. Harayama, Heterocydes 2003, 61, 521-528.
63. L. Hazai, G. Hornyak, ACH Models Chem. 1998, 135, 494-514.
64. a) G. Bringmann, S. Tasler, Tetrahedron 2001, 57, 331-343;
65. b) I. Moreno, I. Tellitu, M. T. Herrero, R. SanMartin, E. Dominguez, Curr. Org. Chem. 2002, 6, 1433-1452;
66. c) H. Hamamoto, G. Anilkumar, H. Tohma, Y. Kita, Chem. Eur. J. 2002, 8, 5377-5383;
67. d) D. Mirk, A. Willner, R. Froehlich, S. R. Waldvogel, Adv. Synth. Catal. 2004, 346, 675-681.
68. a) R. Olivera, R. SanMartin, E. Domínguez, J. Org. Chem. 2000, 65, 7010-7019;
69. b) R. Olivera, R. SanMartin, I. Tellitu, E. Domínguez, Tetrahedron 2002, 58, 3021-3037.
70. a) W. Adam, M. Sauter, Chem. Ber. 1993, 126, 2697-2699;
71. b) M. Schmittel, A. Langels, J. Org. Chem. 1998, 63, 7328-7337.
72. 2 and VOF/TFA: a) D. L. Comins, X. Chen, L. A. Morgan, J. Org. Chem. 1997, 62, 7435-7438;
73. b) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. Int. Ed. 1998, 37, 2700-2704.
74. 3: c) F. Dötz, J. D. Brand, S. Ito, L. Gherghel, K. Müllen, J. Am. Chem. Soc. 2000, 122, 7707-7717.
75. 2: d) D. Planchenault, R. Dhal, Tetrahedron 1995, 51, 1395-1404.
76. 2: e) M. Ihara, Y. Takino, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1988, 29, 4135-4138.
77. 4: f) J. Doussot, A. Guy, C. Ferroud, Tetrahedron Lett. 2000, 41, 2545-2547.
78. 2O: g) T. R. Hoye, M. Chen, B. Hoang, L. Mi, O. P. Priest, J. Org. Chem. 1999, 64, 7184-7201.
79. 2: h) S. Vyskocil, M. Smrcina, M. Lorenc, I. Tislerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. J. Farrugia, P. Kocovsky, J. Org. Chem. 2001, 66, 1359-1365.
80. 2: i) H.-J. Knölker, K. R. Reddy, A. Wagner, Tetrahedron Lett. 1998, 39, 8267-8270.
81. Several benzophenanthrofurans have been prepared, mostly in moderate yields, by photochemical cyclisation of the corresponding diarylbenzofurans, see: a) A. Couture, A. Lablache-Combier, H. Ofenberg, Tetrahedron 1975, 31, 2023-2028;
82. b) C. Galli, P. Gentili, A. Guarnieri, S. Kobayashi, Z. Rappoport, J. Org. Chem. 1998, 63, 9292-9299;
83. c) G. R. Lappin, J. S. Zannucci, J. Org. Chem. 1971, 36, 1808-1811;
84. d) T. Suzuki, T. Kitamura, T. Sonoda, S. Kobayashi, H. Taniguchi, J. Org. Chem. 1981, 46, 5324-5328;
85. e) P. R. West, S. K. Chaudhary, J. M. Vernon, R. H. Mitchell, J. Chem. Soc, Chem. Commun. 1984, 613-614.
86. For another entry to the benzophenanthrofuran system also based on photochemistry, see: f) T. Yamazaki, H. Shechter, Tetrahedron Lett. 1973, 14, 1417-1420.
87. E. Domínguez, E. Ibeas, E. Martínez de Marigorta, J. K. Palacios, R. SanMartin, J. Org. Chem. 1996, 61, 5435-5439.
88. W. Z. Antkoviak, S. Szwarc, Bull. Acad. Pol. Sci. Ser. Sci. Chim. 1979, 27, 109-114.