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http://dx.doi.org/10.5012/bkcs.2007.28.7.1159

Parallel Synthesis of Unsymmetrical trans-Stilbenes  

Cho, Chul-Hee (School of Chemical Engineering & Materials Science, Chung-Ang University)
Park, Kwang-Yong (School of Chemical Engineering & Materials Science, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.28, no.7, 2007 , pp. 1159-1166 More about this Journal
Abstract
New unsymmetrical trans-stilbenes have been prepared by the sequential coupling reactions of bromobenzenesulfonate with formylarylboronic acids, benzylphosphonates and arylmagnesium bromides and characterized. The nickel-catalyzed reactions of stilbenesulfonates with aryl Grignard reagents produced the corresponding stilbenes via the nucleophilic aromatic substitution of the neopentyloxysulfonyl group by aryl nucleophiles. The great chemoselectivity of the alkyloxysulfonyl group allows the stepwise construction of unsymmetrical trans-stilbenes possessing terphenyl moieties. This procedure appears to be a promising and conceptually straightforward route for the parallel synthesis of various unsymmetrical stilbenes as well as other highly conjugated hydrocarbons.
Keywords
Unsymmetrical trans-stilbenes; Stilbenesulfonates; Nickel-catalyst; Cross-coupling;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 7  (Related Records In Web of Science)
Times Cited By SCOPUS : 9
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1 Sengupta, S.; Muhuri, S. Tetrahedron Lett. 2004, 45, 2895   DOI   ScienceOn
2 Ma, D.; Hu, Y.; Zhang, Y.; Wang, L.; Jing, X.; Wang, F.; Lupton, J. M.; Samuel, I. D. W.; Lo, S.-C.; Burn, P. L. Synthetic Metals 2003, 137, 1125   DOI   ScienceOn
3 Lupton, J. M.; Samuel, I. D. W.; Frampton, M. J.; Beavington, R.; Burn, P. L. Adv. Funct. Mater. 2001, 11, 287   DOI   ScienceOn
4 Lupton, J. M.; Hemingway, L. R.; Samuel, I. D. W.; Burn, P. L. J. Mater. Chem. 2000, 10, 867   DOI   ScienceOn
5 Halim, M.; Pillow, J. N. G.; Samuel, I. D. W.; Burn, P. L. Adv. Mater. 1999, 11, 371   DOI   ScienceOn
6 Becker, K. B. Synthesis 1983, 341
7 Eichen, Y.; Nakhmanovich, G.; Gorelik, V.; Epshtein, O.; Poplawski, J. M.; Ehrenfreund, E. J. Am. Chem. Soc. 1998, 120, 10463   DOI   ScienceOn
8 Orsini, F.; Pelizzoni, F.; Bellini, B.; Miglierini, G. Carbohydrate Research 1997, 301, 95   DOI   ScienceOn
9 Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. Tetrahedron Lett. 1993, 34, 1747
10 Diez-Barra, E.; Garcia-Martinez, J. C.; Rodriguez-Lopez, J. Tetrahedron Lett. 1999, 40, 8181
11 Wang, M.; Jin, Y.; Ho, C.-T. J. Agric. Food Chem. 1999, 47, 3974
12 Meier, H.; Dullweber, U. Tetrahedron Lett. 1996, 37, 1191   DOI   ScienceOn
13 Belfield, K. D.; Chinna, C.; Schafer, K. J. Tetrahedron Lett. 1997, 38, 6131   DOI   ScienceOn
14 Jeffery, T.; Ferber, B. Tetrahedron Lett. 2003, 44, 193   DOI   ScienceOn
15 Chavez, D.; Chai, H. B.; Chagwedera, T. E.; Gao, Q.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Kinghorn, A. D. Tetrahedron Lett. 2001, 42, 3685   DOI   ScienceOn
16 Dai, J. R.; Hallock, Y. F.; Cardellina, II, J. H.; Boyd, M. R. J. Nat. Prod. 1998, 61, 351   DOI   ScienceOn
17 Huang, K.-S.; Li, R.-L.; Wang, Y.-H.; Lin, M. Planta. Med. 2001, 67, 61
18 Savouret, J. F.; Quesne, M. Biomed. Pharmacother. 2002, 56, 84   DOI   ScienceOn
19 Gusman, J.; Malonne, H.; Atassi, G. Carcinogenesis 2001, 22, 1111   DOI   ScienceOn
20 Fremont, L. Life Sci. 2000, 66, 663   DOI   ScienceOn
21 Momotake, A.; Arai, T. J. Photochem. Photobiol. A: Photochem. Reviews 2004, 5, 1   DOI   ScienceOn
22 Imai, M.; Arai, T. Tetrahedron Lett. 2002, 43, 5265   DOI   ScienceOn
23 Meier, H. Angew. Chem., Int. Ed. 1992, 31, 1399   DOI
24 Waldeck, D. H. Chem. Rev. 1991, 91, 415   DOI
25 Dottinger, S. E.; Hohloch, M.; Hohnholz, D.; Segura, J. L.; Steinhuber, E.; Hanack, M. Synth. Met. 1997, 84, 267   DOI   ScienceOn
26 Iliya, I.; Ali, Z.; Tanaka, T.; Iinuma, M.; Furusawa, M.; Nakaya, K.-i.; Murata, J.; Darnaedi, D.; Matsuura, N.; Ubukata, M. Phytochemistry 2003, 62, 601   DOI   ScienceOn
27 Sengupta, S.; Sadhukhan, S. K.; Singh, R. S.; Pal, N. Tetrahedron Lett. 2002, 43, 1117   DOI   ScienceOn
28 Guiso, M.; Marra, C.; Farina, A. Tetrahedron Lett. 2002, 43, 597   DOI   ScienceOn
29 Bazan, G. C.; Oldham, Jr. W. J.; Lachicotte, R. J.; Tretiak, S.; Chernyak, V.; Mukamel, S. J. Am. Chem. Soc. 1998, 120, 9188   DOI   ScienceOn
30 Kiji, J.; Okano, T.; Ooue, A. J. Mol. Catal. A: Chem. 1999, 147, 3   DOI   ScienceOn
31 Spencer, A. J. Organomet. Chem. 1983, 247, 117   DOI   ScienceOn
32 Tietze, L. F.; Kettschau, G.; Heuschert, U.; Nordmann, G. Chem. Eur. J. 2001, 7, 368   DOI   ScienceOn
33 Tietze, L. F.; Nordmann, G. Synlett 2001, 337
34 Maddux, T.; Li, W.; Yu, L. J. Am. Chem. Soc. 1997, 119, 844   DOI   ScienceOn
35 Solladie, G.; Pasturel-Jacope, Y.; Maignan, J. Tetrahedron 2003, 59, 3315   DOI   ScienceOn
36 Liu, K. H.; Masuda, A.; Yamazaki, Y. Tetrahedron Lett. 1975, 3007
37 Treves, G. R. J. Am. Chem. Soc. 1948, 70, 875   DOI
38 Hauser, C. R.; Brasen, W. R.; Skell, P. S.; Kantor, S. W.; Brodhag, A. E. J. Am. Chem. Soc. 1956, 78, 1653   DOI
39 McMurry, J. E.; Fleming, M. P. J. Am. Chem. Soc. 1974, 96, 4708   DOI
40 Cho, C.-H.; Sun, M.; Park, K. Bull. Korean Chem. Soc. 2005, 26, 1410   DOI   ScienceOn
41 Cho, C.-H.; Kim, I.-S.; Park, K. Tetrahedron 2004, 70, 4589
42 Cho, C.-H.; Yun, H.-S.; Park, K. J. Org. Chem. 2003, 68, 3017   DOI   ScienceOn
43 Cho, C.-H.; Kim, C.-B.; Sun, M.; Park, K. Bull. Korean Chem. Soc. 2003, 24, 1632   DOI   ScienceOn
44 Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1997, 275, 218   DOI
45 Ducrot, P.-H.; Kollmann, A.; Bala, A. E.; Majira, A.; Kerhoas, L.; Delorme, R.; Einhorn, J. Tetrahedron Lett. 1998, 39, 9655
46 Feringa, L.; Jager, W. F.; de Lange, B. Tetrahedron 1993, 49, 8267   DOI   ScienceOn
47 Emmelius, M.; Pawlowski, G.; Vollmann, H. W. Angew. Chem. Int. Ed. 1989, 28, 1445   DOI
48 Marder, S. R.; Kippelen, B.; Jen, A. K.-Y.; Peyghambarian, N. Nature 1997, 388, 845
49 Ashwell, G. J.; Jefferies, G.; Hamilton, D. G.; Lynch, D. E.; Roberts, M. P. S.; Bahra, G. S.; Brown, C. R. Nature 1995, 375, 385   DOI   ScienceOn
50 Chen, C.-T.; Marder, S. R.; Cheng, L.-T. J. Chem. Soc., Chem. Commun. 1994, 259
51 Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Medray, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539   DOI
52 Jin, Y.; Kim, J.; Park, S. H.; Kim, H.; Lee, K.; Suh, H. Bull. Korean Chem. Soc. 2005, 26, 1807   DOI   ScienceOn
53 Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. Int. Ed. 1998, 37, 402   DOI   ScienceOn
54 Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477   DOI   ScienceOn
55 Burns, P. L.; Holmes, A. B.; Kraft, A.; Bradley, D. D. C.; Brown, A. R.; Friend, R. H. Nature 1992, 356, 47   DOI
56 Hohnholz, D.; Schweikart, K.-H.; Subramanian, L. R.; Wedel, A.; Wischert, W.; Hanack, M. Synth. Met. 2000, 110, 141
57 Lipiñski, J.; Bartkowiak, W. Chem. Phys. 1999, 245, 263   DOI   ScienceOn
58 Kim, H. K.; Moon, I. K.; Lee, H.-J.; Han, S.-G.; Won, Y. H. Polymer 1998, 39, 1719
59 Romaniello, P.; Lelj, F. J. Fluorine Chem. 2004, 125, 145   DOI   ScienceOn
60 Papagni, A.; Maiorana, S.; Del Buttero, P.; Perdicchia, D.; Cariati, F.; Cariati, E.; Marcolli, W. Eur. J. Org. Chem. 2002, 8, 1380
61 Walter, G.; Liebl, R.; Von Angerer, E. Bioorg. Med. Chem. 2004, 14, 4659   DOI   ScienceOn
62 Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350   DOI   ScienceOn
63 Hohloch, M.; Segura, J. L.; Doettinger, S. E.; Hohnholz, D.; Steinhuber, E.; Spreitzer, H.; Hanack, M. Synth. Met. 1997, 84, 319   DOI   ScienceOn
64 Mooney III, W. F.; Brown, P. E.; Russell, J. C.; Costa, S. B.; Pedersen, L. G.; Whitten, D. G. J. Am. Chem. Soc. 1984, 106, 5659   DOI   ScienceOn
65 Um, S.-I.; Lee, J.-K.; Kang, Y.; Baek, D.-J. Dyes Pigments 2005, 64, 93   DOI   ScienceOn
66 Sengupta, S. Tetrahedron Lett. 2003, 44, 307   DOI   ScienceOn
67 Sigalov, M.; Ben-Asuly, A.; Shapiro, L.; Ellern, A.; Khodorkovsky, V. Tetrahedron Lett. 2000, 41, 8573
68 Xu, Q.; Chen, H. Z.; Wang, M. Mater. Chem. Phys. 2004, 87, 446   DOI   ScienceOn
69 Zhan, C.; Cheng, Z.; Zheng, J.; Zhang, W.; Xi, Y.; Qin, J. J. Appl. Polym. Sci. 2002, 85, 2718   DOI   ScienceOn
70 Yang, J.; Lin, H.; Zheng, M.; Bai, F. Macromol. Chem. Phys. 2001, 202, 2287   DOI   ScienceOn
71 Markham, J. P. J.; Namdas, E. B.; Anthopoulos, T. D.; Samuel, I. D. W.; Richards, G. J.; Burn, P. L. Appl. Phys. Lett. 2004, 85, 1463   DOI   ScienceOn
72 Stanfield, J. A.; Reynolds, Jr., L. B. J. Am. Chem. Soc. 1952, 74, 2878   DOI
73 Cho, C.-H.; Sun, M.; Seo, Y.-S.; Kim, C.-B.; Park, K. J. Org. Chem. 2005, 70, 1482   DOI   ScienceOn
74 Behnisch, B.; Hanack, M. Synthetic Metals 2001, 121, 1661   DOI   ScienceOn
75 Wadsworth, D. H.; Schupp, III, O. E.; Seus, E. J.; Ford, Jr., J. A. J. Org. Chem. 1965, 30, 680   DOI
76 Wadsworth, Jr., W. S.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733   DOI