396
A. V. Bedekar et al. / Tetrahedron Letters 54 (2013) 392–396
19. (a) Mallory, F. B.; Mallory, C. W. J. Org. Chem. 1983, 48, 526; (b) Weis, U.;
Acknowledgment
Andersson, J. T. Polycyclic Aromat. Compd. 2002, 22, 71.
20. Li, S.; Xiang, J.; Mei, X.; Xu, C. Tetrahedron Lett. 2008, 49, 1690.
21. Amsharov, K. Y.; Kabdulov, M. A.; Jansen, M. Eur. J. Org. Chem. 2009, 6328.
22. Chaudhary, A. R.; Bedekar, A. V. Synth. Commun. 2012, 42, 1778.
23. (a) Saiyed, A. S.; Bedekar, A. V. Tetrahedron Lett. 2010, 51, 6227; (b) Saiyed, A. S.;
Patel, K. N.; Kamath, B. V.; Bedekar, A. V. Tetrahedron Lett. 2012, 53, 4692.
24. (a) Harvey, F. R. Polycyclic Aromatic Hydrocarbons; Wiley-VCH: New York, 1997;
(b) Shen, Y.; Chen, C.-F. Chem. Rev. 2012, 112, 1463.
25. (a) Talele, H. R.; Gohil, M. J.; Bedekar, A. V. Bull. Chem. Soc. Jpn. 2009, 82, 1182;
(b) Talele, H. R.; Chaudhary, A. R.; Patel, P. R.; Bedekar, A. V. ARKIVOC 2011, ix,
15.
Financial support for this work by the Council of Scientific and
Industrial Research (CSIR), New Delhi [No. 01(2386)/10/EMR-II] is
gratefully acknowledged. We also thank CSIR, New Delhi for the
award of research fellowship to ARC, Navin Fluorine International
Limited for providing samples of fluorinated reagents and Profes-
sor B.V. Kamath, Head, Department of Chemistry for the infrastruc-
tural facilities and constant encouragements.
26. A similar observation was reported earlier, see Ref. 25a.
27. Renak, M. L.; Bartholomew, G. P.; Wang, S.; Ricatto, P. J.; Lachicotte, R. J.; Bazan,
G. C. J. Am. Chem. Soc. 1999, 121, 7787.
References and notes
28. Chang, C. –S.; Wu, Y. –T. Sci. Synth. 2010, 955.
1. (a) Sardella, D. J.; Mahathalang, P.; Mariani, H. A.; Boger, E. J. Org. Chem. 1980,
45, 2064; (b) Boger, E.; O’Malley, R. F.; Sardella, D. J. J. Fluorine Chem. 1976, 8,
513.
29. (a) Winter, W.; Langjahr, U.; Meier, H.; Merkushev, E. B.; Yur´ev, Y. G. Chem. Ber.
1984, 117, 2452; (b) Erickson, M. S.; Miliken, J. Polycyclic Aromat. Compd. 1996,
8, 1; (c) Hagen, S.; Scott, L. T. J. Org. Chem. 1996, 61, 7198.
2. (a) Hecht, S. S.; Loy, M.; Mazzaresa, R.; Hoffmann, D. J. J. Med. Chem. 1978, 21,
38; (b) Black, S. D.; Sharma, P. K.; Gallucci, J. D.; Blackburn, A. C.; Downs, J. W.;
Rinderle, S. J.; Witiak, D. T. Carcinogenesis 1992, 13, 1337; (c) Harvey, R. G.;
Dunne, F. B. Science 1978, 273, 566; (d) Bernard Daniel, F.; Cazer, F. D.;
D’Ambrosio, S. M.; Hart, R. W.; Kim, W. H.; Witiak, D. T. Cancer Lett. 1979, 6,
263; (e) Witiak, D. T.; Goswami, S.; Milo, G. E. J. Org. Chem. 1988, 53, 345.
3. (a) Yagi, H.; Thakker, D. R.; Levin, W.; Jerina, D. M. J. Am. Chem. Soc. 1987, 109,
838; (b) Baer-Dubowski, W.; Nair, R. V.; Dubowski, A.; Harvey, R. G.; Cortez, C.;
DiGiovanni, J. Chem. Res. Toxicol. 1996, 9, 722.
4. Hecht, S. S.; Hirota, N.; Loy, M.; Hoffmann, D. Cancer Res. 1978, 38, 1694.
5. (a) Cremonesi, P.; Stack, D. E.; Rogan, E. G.; Cavelieri, E. L. J. Org. Chem. 1994, 59,
7683; (b) Cremonesi, P.; Cavalieri, E. L.; Rogan, E. G. J. Org. Chem. 1989, 54, 3561.
6. Loo, Y. –L.; Hiszpanski, A. M.; Kim, B.; Wei, S.; Chiu, C. –Y.; Steigerwald, M. L.;
Nuckolls, C. Org. Lett. 2010, 12, 4840.
7. (a) Okazaki, T.; Laali, K. K. Adv. Org. Synth. 2006, 2, 353; (b)Fluorine in Medicinal
Chemistry and Chemical Biology; Ojima, I., Ed.; Wiley: New York, 2009; (c)
Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev.
2011, 40, 3496; (d) Salwiczek, M.; Nyakatura, E. K.; Gerling, U. I. M.; Ye, S.;
Koksch, B. Chem. Soc. Rev. 2012, 41, 2135.
8. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37,
320.
9. Hird, M. Chem. Soc. Rev. 2007, 36, 2070.
30. Representative procedure for the one pot Wittig–Heck reaction:
E-2-[2-(4-Fluorophenyl)vinyl]naphthalene (18):
In dry N2 flushed two-necked r.b. flask a mixture of p-bromofluorobenzene
(0.50 g,
triphenylmethylphosphonium iodide (1.73 g, 4.286 mmol), palladium acetate
(0.0032 g, 0.014 mmol) and (0.0055 mg, 0.017 mmol), TBAB (0.184 g,
0.571 mmol), and K2CO3 (1.591 g, 11.43 mmol) in dry N,N-
2.857 mmol),
2-naphthaldehyde
(0.67 g,
4.286 mmol),
L
dimethylacetamide (20 mL) was taken and kept under N2 atmosphere. The
reaction mixture heated to 140 °C for 40 h. The cooled mixture was then
poured into water (25 mL) and extracted with ethyl acetate (3 ꢀ 25 mL). The
combined organic layer was washed with water (2 ꢀ 20 mL), dried with
anhydrous sodium sulfate, concentrated in vacuum and purified by column
chromatography over silica gel and petroleum ether as eluent to give E-2-[2-
(4-fluorophenyl)vinyl]naphthalene 18 as white solid (0.428 g, 61%); mp 148–
150 °C (Lit.21 151–152 °C).
1H NMR (CDCl3, 400 MHz) d 7.89–7.83 (m, 4H), 7.77–7.74 (dd, J = 8.8, 1.6 Hz,
1H), 7.6–7.46 (m, 4H), 7.22 (s, 2H), 7.12–7.07 (m, 2H).
Mass (EI) 248.5 (M)+ (40), 247.8 (98), 247 (55), 246 (100), 245 (39), 229 (23).
IR (KBr) 3051, 3017, 2926, 2354, 1897, 1666, 1596, 1509, 1411, 1238, 1158,
1097, 966, 903, 855, 826, 740, 694, 641 cmꢁ1
.
General procedure for photodehydrocyclization:
2-Fluorobenzo[c] phenanthrene (30):
10. Reichenbächer, K.; Süss, H. I.; Hulliger, J. Chem. Soc. Res. 2005, 34, 22.
11. (a) Chambers, R. D. In Fluorine in Organic Chemistry; Olah, G. A., Ed.; Wiley
Interscience: New York, 1973; (b) Hudlicky´, M. Fluorine Chemistry for Organic
Chemists; Oxford University Press: New York, 2000; (c) Hiyama, T. In
Organofluorine Compounds: Chemistry and Applications; Yamamto, H., Ed.;
Springer: Berlin, 2000; (d) Kirsch, P. Modern Fluoroorganic Chemistry:
Synthesis, Reactivity Applications; Wiley-VCH: Weinheim, 2004.
12. (a) Mann, J. Chem. Soc. Rev. 1987, 16, 381; (b) Rozen, S. Acc. Chem. Res. 1988, 21,
307; (c) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737; (d) Adams,
D. J.; Clark, J. H. Chem. Soc. Rev. 1999, 28, 225; (e) Singh, R. P.; Shreeve, J. M. Acc.
Chem. Res. 2004, 37, 31; (f) Ma, J. –A.; Cahard, D. Chem. Rev. 2004, 104, 6119; (g)
Wang, Y.; Burton, D. J. Tetrahedron Lett. 2006, 47, 9279. and the references cited
therein.
To
a
solution of E-2-[2-(4-fluorophenyl)vinyl]naphthalene 18 (0.20 g,
0.806 mmol) in toluene (550 mL) was added iodine (225 mg, 0.887 mmol)
and dry tetrahydrofuran (6.6 mL, 80.64 mmol) in a standerd immersion photo
reactor. The mixture is degassed (15 min.) by sonication and irradiated with
125 W high pressure mercury vapor lamp for 24 h. The reaction mixture was
washed with aquous sodium thiosulfate (3 ꢀ 150 mL), dried over anhydrous
sodium sulfate. The solvent was removed under reduced pressure. The residue
was chromatograhed on silica gel column by eluting with petroleum ether to
afford 2-fluorobenzo[c]phenanthrene 30 as white solid (0.14 g, 71%), mp 64–
66 °C (Lit.31 63.7–64.1 °C).
1H NMR (400 MHz, CDCl3)
d 9.09–9.07 (d, J = 8.4 Hz, 1H), 8.84–8.80 (dd,
J = 12.4, 2.4 Hz, 1H), 8.05–8.99 (m, 2H), 7.94–7.89 (m, 2H), 7.85–7.79 (m, 2H),
7.74–7.69 (m, 1H), 7.68–7.63 (m, 1H), 7.43–7.38 (td, J = 8.8, 2.8 Hz, 1H).
Mass (EI) 246.3 (100), 245.2 (93), 243.8 (80), 241.7 (15), 228.3 (20), 227.2 (20),
226.1(18), 225.2 (11), 121.9 (60), 113.1 (12), 112.1 (11), 110.1 (11), 98.7 (10).
13. Laali, K. K.; Tanaka, M.; Forohar, F.; Cheng, M.; Fetzer, J. C. J. Fluorine Chem.
1998, 91, 185.
14. Filler, R. Isr. J. Chem. 1978, 17, 71.
15. Rozen, S. Chem. Rev. 1996, 96, 1717.
16. Laali, K. K.; Hansen, P. E. J. Org. Chem. 1993, 58, 417.
IR (KBr)
1124, 1010, 974, 885, 837, 784, 744 cmꢁ1
31. Ittah, Y.; Jerina, D. M. J. Fluorine Chem. 1980, 16, 137.
t 3046, 1684, 1598, 1499, 1429, 1357, 1289, 1247, 1216, 1199, 1176,
.
17. Bernstein, W. J.; Calvin, M.; Buchardt, O. J. Am. Chem. Soc. 1973, 95, 527.
18. Sardella, D. J.; Ghoshal, P. K.; Boger, E. J. Fluorine Chem. 1982, 20, 459.