Domino Friedel-crafts-type cyclizations of difluoroalkenes promoted by the α-cation-stabilizing effect of fluorine: An efficient method for synthesizing angular PAHs

Chemistry - A European Journal

Volumn 17, Issue 43, 2011, Pages 12175-12185

  Fuchibe, Kohei ^a   Jyono, Hideharu ^b   Fujiwara, Masaki ^b   Kudo, Takao ^b   Yokota, Misaki ^c   Ichikawa, Junji ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

carbocations; domino reactions; fluorine; helicenes; PAHs

Indexed keywords

1 ,1-DIFLUOROALK-1-ENES; ARYL SUBSTITUENTS; CAMPHORSULFONIC ACID; CARBOCATIONS; CARBOCYCLES; CARBON ATOMS; CYCLIZATIONS; DOMINO CYCLIZATIONS; DOMINO REACTIONS; EFFICIENT METHOD; ELECTRON-RICH; HELICENES; HIGH YIELD; PAHS; PROTONATED; RING SYSTEMS; TRIFLUOROMETHANE SULFONIC ACID;

FLUORINE; OLEFINS; POLYCYCLIC AROMATIC HYDROCARBONS; PROTONATION; REACTION KINETICS; SUBSTITUTION REACTIONS;

CYCLIZATION;

EID: 80054035892     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100618     Document Type: Article

References (124)

1. R. G. Harvey, Polycyclic Aromatic Hydrocarbons, Wiley, New York, 1997
2. J. C. Fetzer, Large (C>=24) Polycyclic Aromatic Hydrocarbons: Chemistry and Analysis, Wiley, New York, 2000
3. W. H. Laarhoven, W. J. C. Prinsen, Top. Curr. Chem. 1984, 125, 63-130
4. K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76.
5. S. Sahasithiwat, T. Mophuang, L. Menbangpung, S. Kamtonwong, T. Sooksimuang, Synth. Met. 2010, 160, 1148-1152.
6. M. T. Reetz, E. W. Beuttenmüller, R. Goddard, Tetrahedron Lett. 1997, 38, 3211-3214
7. N. Takenaka, R. S. Sarangthem, B. Captain, Angew. Chem. 2008, 120, 9854-9856
8. Angew. Chem. Int. Ed. 2008, 47, 9708-9710.
9. J.-Y. Wang, Y. Zhou, J. Yan, L. Ding, Y. Ma, Y. Cao, J. Wang, J. Pei, Chem. Mater. 2009, 21, 2595-2597
10. H. Okamoto, N. Kawasaki, Y. Kaji, Y. Kubozono, A. Fujiwara, M. Yamaji, J. Am. Chem. Soc. 2008, 130, 10470-10471.
11. A. S. Ionkin, W. J. Marshall, B. M. Fish, L. M. Bryman, Y. Wang, Chem. Commun. 2008, 2319-2321.
12. U. Scherf, E. J. W. List, Adv. Mater. 2002, 14, 477-487
13. Y. Ohmori, M. Uchida, K. Muro, K. Yoshino, Jpn. J. Appl. Phys. 1991, 30, L1941-L1943.
14. J. Ichikawa, H. Jyono, T. Kudo, M. Fujiwara, M. Yokota, Synthesis 2005, 39-46.
15. Organofluorine Chemistry: Principles and Commercial Applications (Eds.:, R. E. Banks, B. E. Smart, J. C. Tatlow,), Plenum, New York, 1994.
16. G. A. Olah, R. H. Schlosberg, J. Am. Chem. Soc. 1968, 90, 2726-2727
17. G. A. Olah, Angew. Chem. 1995, 107, 1519-1532
18. Angew. Chem. Int. Ed. Engl. 1995, 34, 1393-1405. See also
19. B. J. Dahl, N. S. Mills, J. Am. Chem. Soc. 2008, 130, 10179-10186
20. K. K. Laali, D. S. Nagvekart, J. Org. Chem. 1991, 56, 1867-1874.
21. A. D. Allen, T. T. Tidwell, in Progress in Carbocation Chemistry, Vol. 1 (Ed.:, X. Creary,), JAI, London, 1989, pp. 1-44
22. C. G. Krespan, V. A. Petrov, Chem. Rev. 1996, 96, 3269-3302. See also
23. G. A. Olah, Y. K. Mo, J. Org. Chem. 1972, 37, 1028-1034.
24. F. Tian, M. A. Battiste, W. R. Dolbier, Jr., Org. Lett. 1999, 1, 193-196
25. M. McAllister, T. T. Tidwell, M. R. Peterson, I. G. Csizmadia, J. Org. Chem. 1991, 56, 575-580
26. L. D. Kispert, C. U. Pittman Jr., D. L. Allison, T. B. Patterson, Jr., C. W. Gilbert, Jr., C. F. Hains, J. Prather, J. Am. Chem. Soc. 1972, 94, 5979-5985.
27. P. V. Fish, W. S. Johnson, G. S. Jones, F. S. Tham, R. K. Kullnig, J. Org. Chem. 1994, 59, 6150-6152
28. T. Morikawa, I. Kumadaki, M. Shiro, Chem. Pharm. Bull. 1985, 33, 5144-5146
29. W. S. Johnson, T. A. Lyle, G. W. Daub, J. Org. Chem. 1982, 47, 161-163
30. W. S. Johnson, G. W. Daub, T. A. Lyle, M. Niwa, J. Am. Chem. Soc. 1980, 102, 7800-7802.
31. M. Yokota, D. Fujita, J. Ichikawa, Org. Lett. 2007, 9, 4639-4642
32. H. Tanabe, J. Ichikawa, Chem. Lett. 2010, 39, 248-249.
33. Clasification of reaction integration, including domino reactions, is schematically described:, S. Suga, D. Yamada, J.-I. Yoshida, Chem. Lett. 2010, 39, 404-406.
34. J. Ichikawa, M. Yokota, T. Kudo, S. Umezaki, Angew. Chem. 2008, 120, 4948-4951
35. Angew. Chem. Int. Ed. 2008, 47, 4870-4873; and references therein.
36. J. Ichikawa, J. Fluorine Chem. 2000, 105, 257-263
37. J. Ichikawa, T. Sonoda, H. Kobayashi, Tetrahedron Lett. 1989, 30, 6379-6382
38. J. Ichikawa, C. Ikeura, T. Minami, Synlett 1992, 739-740; see also
39. J. Ichikawa, T. Minami, T. Sonoda, H. Kobayashi, Tetrahedron Lett. 1992, 33, 3779-3782
40. J. Ichikawa, C. Ikeura, T. Minami, J. Fluorine Chem. 1993, 63, 281-285.
41. R. Ocampo, W. R. Dolbier, Jr., R. Paredes, J. Fluorine Chem. 1998, 88, 41-50
42. W. R. Dolbier, Jr., R. Ocampo, J. Org. Chem. 1995, 60, 5378-5379.
43. J.-P. Bégué, D. Bonnet-Delpon, M. H. Rock, J. Chem. Soc. Perkin Trans. 1 1996, 1409-1413. See also
44. D. A. Kendrick, M. Kolb, J. Fluorine Chem. 1989, 45, 265-272
45. J.-P. Bégué, D. Bonnet-Delpon, M. H. Rock, Synlett 1995, 659-660
46. J. Ichikawa, Y. Iwai, R. Nadano, T. Mori, M. Ikeda, Chem. Asian J. 2008, 3, 393-406. For 2-trifluoromethylallylsilane required for preparation of 4, see
47. T. Yamazaki, N. Ishikawa, Chem. Lett. 1984, 13, 521-524.
48. J.-P. Bégué, D. Bonnet-Delpon, B. Crousse, Synlett 2004, 18-29
49. I. A. Shuklov, N. V. Dubrovina, A. Börner, Synthesis 2007, 2925-2943. For recent reports, see
50. N. Nishiwaki, R. Kamimura, K. Shono, T. Kawakami, K. Nakayama, K. Nishino, T. Nakayama, K. Takahashi, A. Nakamura, T. Hosokawa, Tetrahedron Lett. 2010, 51, 3590-3592
51. A. Saito, J. Kasai, T. Konishi, Y. Hanzawa, J. Org. Chem. 2010, 75, 6980-6982
52. A. Saito, A. Kanno, Y. Hanzawa, Angew. Chem. 2007, 119, 4005-4007
53. Angew. Chem. Int. Ed. 2007, 46, 3931-3933
54. A. Berkessel, J. A. Adrio, J. Am. Chem. Soc. 2006, 128, 13412-13420.
55. Compound 5 a can also be synthesized by super acid-promoted skeletal rearrangent of 1,1′-Bi(benzocyclobutenylidene)s:, K. K. Laali, T. Okazaki, S. D. Bunge, D. Lenoir, J. Org. Chem. 2008, 73, 4092-4100.
56. V. Gold, K. K. Laali, K. P. Morris, L. Z. Zdunek, J. Chem. Soc. Chem. Commun. 1981, 769-771.
57. Strain energies were estimated by calculating heat of hydrogenolysis of two C(Ar)-C(alkene) bonds of 5 (B3LYP/6-31G*). For a ring strain of cycloalkanes, see:, E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
58. A. Marsili, M. Isola, Tetrahedron 1967, 23, 1037-1041
59. A. Marsili, M. Isola, Tetrahedron Lett. 1965, 6, 3023-3026.
60. W. H. Laarhoven, J. A. M. van Broekhoven, Tetrahedron Lett. 1970, 11, 73-76
61. W. H. Laarhoven, Th. J. H. M. Cuppen, R. J. F. Nivard, Tetrahedron 1970, 26, 4865-4881.
62. M. Flammang-Barbieux, J. Nasielski, R. H. Martin, Tetrahedron Lett. 1967, 8, 743-744
63. L. Liu, B. Yang, T. J. Katz, M. K. Poindexter, J. Org. Chem. 1991, 56, 3769-3775. Recent reports
64. F. Aloui, R. E. Abed, A. Marinetti, B. B. Hassine, Tetrahedron Lett. 2007, 48, 2017-2020
65. R. El Abed, F. Aloui, J.-P. Genêt, B. B. Hassine, A. Marinetti, J. Organomet. Chem. 2007, 692, 1156-1160.
66. M. C. Carreño, Á. Enríquez, S. García-Cerrada, M. J. Sanz-Cuesta, A. Urbano, F. Maseras, A. Nonell-Canals, Chem. Eur. J. 2008, 14, 603-620
67. M. del Mar Real, J. P. Sestelo, L. A. Sarandeses, Tetrahedron Lett. 2002, 43, 9111-9114
68. K. Paruch, T. J. Katz, C. Incarvito, K.-C. Lam, B. Rhatigan, A. L. Rheingold, J. Org. Chem. 2000, 65, 7602-7608
69. T. J. Katz, L. Liu, N. D. Willmore, J. M. Fox, A. L. Rheingold, S. Shi, C. Nuckolls, B. H. Rickman, J. Am. Chem. Soc. 1997, 119, 10054-10063. Synthesis of optically active helicene derivatives
70. M. C. Carreño, S. García-Cerrada, A. Urbano, J. Am. Chem. Soc. 2001, 123, 7929-7930.
71. D. C. Harrowven, I. L. Guy, L. Nanson, Angew. Chem. 2006, 118, 2300-2303
72. Angew. Chem. Int. Ed. 2006, 45, 2242-2245
73. D. C. Harrowven, M. I. T. Nunn, D. R. Fenwick, Tetrahedron Lett. 2002, 43, 3189-3191
74. D. C. Harrowven, M. I. T. Nunn, D. R. Fenwick, Tetrahedron Lett. 2002, 43, 7345-7347.
75. S. K. Collins, A. Grandbois, M. P. Vachon, J. CÃté, Angew. Chem. 2006, 118, 2989-2992
76. Angew. Chem. Int. Ed. 2006, 45, 2923-2926.
77. K. Kamikawa, I. Takemoto, S. Takemoto, H. Matsuzaka, J. Org. Chem. 2007, 72, 7406-7408.
78. D. Peña, A. Cobas, D. Pérez, E. Guitián, L. Castedo, Org. Lett. 2003, 5, 1863-1866
79. Y. Ogawa, M. Toyama, M. Karikomi, K. Seki, K. Haga, T. Uyehara, Tetrahedron Lett. 2003, 44, 2167-2170
80. M. Gingras, F. Dubois, Tetrahedron Lett. 1999, 40, 1309-1312
81. Z. Y. Wang, J. E. Douglas, Macromolecules 1997, 30, 8091-8093
82. S. Kumar, J. Org. Chem. 1997, 62, 8535-8539.
83. A. Urbano, Angew. Chem. 2003, 115, 4116-4119
84. Angew. Chem. Int. Ed. 2003, 42, 3986-3989
85. T. J. Katz, Angew. Chem. 2000, 112, 1997-1999
86. Angew. Chem. Int. Ed. 2000, 39, 1921-1923
87. H. Suzuki, H. Osuga, J. Synth. Org. Chem. Jpn. 1994, 52, 1020-1031
88. R. H. Martin, Angew. Chem. 1974, 86, 727-738
89. Angew. Chem. Int. Ed. Engl. 1974, 13, 649-660.
90. F. TeplÃ, I. G. Stará, I. StarÃ, A. Kollárovič, D. Luštinec, Z. Krausová, D. Åaman, P. Fiedler, Eur. J. Org. Chem. 2007, 4244-4250
91. I. StarÃ, I. G. Stará, Z. Alexandrová, P. Sehnal, F. TeplÃ, D. Åaman, L. Rulíšek, Pure Appl. Chem. 2006, 78, 495-499
92. F. TeplÃ, I. G. Stará, I. StarÃ, A. Kollárovič, D. Åaman, Å. Vyskoil, P. Fiedler, J. Org. Chem. 2003, 68, 5193-5197
93. F. TeplÃ, I. G. Stará, I. StarÃ, A. Kollárovič, D. Åaman, L. Rulíšek, P. Fiedler, J. Am. Chem. Soc. 2002, 124, 9175-9180.
94. See also:, Y. Zhang, J. L. Petersen, K. K. Wang, Org. Lett. 2007, 9, 1025-1028.
95. P. Sehnal, Z. Krausová, F. TeplÃ, I. G. Stará, I. StarÃ, L. Rulíšek, D. Åaman, I. CísaÅ ová, J. Org. Chem. 2008, 73, 2074-2082
96. K. Tanaka, A. Kamisawa, T. Suda, K. Noguchi, M. Hirano, J. Am. Chem. Soc. 2007, 129, 12078-12079. [Thia variants]
97. A. Rajca, S. Rajca, M. Pink, M. Miyasaka, Synlett 2007, 1799-1822
98. A. Bossi, S. Maiorana, C. Graiff, A. Tiripicchio, E. Licandro, Eur. J. Org. Chem. 2007, 4499-4509
99. S. K. Collins, M. P. Vachon, Org. Biomol. Chem. 2006, 4, 2518-2524
100. K. E. S. Phillips, T. J. Katz, S. Jockusch, A. J. Lovinger, N. J. Turro, J. Am. Chem. Soc. 2001, 123, 11899-11907
101. T. Caronna, R. Sinisi, M. Catellani, L. Malpezzi, S. V. Meille, A. Mele, Chem. Commun. 2000, 1139-1140. [Aza variants]
102. J. Míšek, F. TeplÃ, I. G. Stará, M. TichÃ, D. Åaman, I. CísaÅová, P. Vojtíšek, I. StarÃ, Angew. Chem. 2008, 120, 3232-3235
103. Angew. Chem. Int. Ed. 2008, 47, 3188-3191.
104. It has been known that the treatment of 1 p with polyphosphoric acid or HF induced double cyclization but a sequential Wagner-Meerwein rearrangement gave tetrahydrochrysene, not [4]helicene:, E. Cahana, G. Schmidt, K. Shah, J. Org. Chem. 1959, 24, 557-559.
105. For a review on perfluorinated allylcations, see:, G. G. Belen'kii, J. Fluorine Chem. 1996, 77, 107-116.
106. Y. Kobayashi, T. Nagai, I. Kumadaki, M. Takahashi, T. Yamauchi, Chem. Pharm. Bull. 1984, 32, 4382-4387; see also
107. H. Takusari, S. Okazaki, Chem. Lett. 1984, 13, 885-888
108. F. Gyenes, S. T. Purrington, Y.-S. Liu, J. Org. Chem. 1999, 64, 1366-1368.
109. A. Riahi, C. Thorey, F. Hénin, J. Muzart, Synth. Commun. 1998, 28, 4339-4344
110. J. A. Vale, D. F. Zanchetta, P. J. S. Moran, J. A. R. Rodrigues, Synlett 2009, 75-78. See also
111. K. Adachi, M. Mori, Bull. Chem. Soc. Jpn. 1983, 56, 651-652.
112. H. Isobe, S. Hitosugi, T. Matsuno, T. Iwamoto, J. Ichikawa, Org. Lett. 2009, 11, 4026-4028. For other synthetic use of 3, see
113. H. Zhang, C.-B. Zhou, Q.-Y. Chen, J.-C. Xiao, R. Hong, Org. Lett. 2011, 13, 560-563
114. T. M. Gøgsig, L. S. Søbjerg, A. T. Lindhardt, K. L. Jensen, T. Skrydstrup, J. Org. Chem. 2008, 73, 3404-3410
115. K. Tanaka, T. Nakai, N. Ishikawa, Tetrahedron Lett. 1978, 19, 4809-4810.
116. J.-Q. Wang, E. H. Weyand, R. G. Harvey, J. Org. Chem. 2002, 67, 6216-6219.
117. X. Cheng, S.-F. Zhu, X.-C. Qiao, P.-C. Yan, Q.-L. Zhou, Tetrahedron 2006, 62, 8077-8082
118. X. Cheng, G.-H. Hou, J.-H. Xie, Q.-L. Zhou, Org. Lett. 2004, 6, 2381-2383
119. G. A. Olah, T. Mathew, M. Farnia, G. K. S. Prakash, Synlett 1999, 1067-1068.
120. S. J. Hwang, H. J. Kim, S. Chang, Org. Lett. 2009, 11, 4588-4591.
121. M. Topolski, J. Org. Chem. 1995, 60, 5588-5594.
122. H.-C. Shen, J.-M. Tang, H.-K. Chang, C.-W. Yang, R.-S. Liu, J. Org. Chem. 2005, 70, 10113-10116.
123. E. Fillion, D. Fishlock, A. Wilsily, J. M. Goll, J. Org. Chem. 2005, 70, 1316-1327.
124. A. L. Rodriguez, T. Bunlaksananusorn, P. Knochel, Org. Lett. 2000, 2, 3285-3287.