Palladium-catalyzed dimerization of conjugated diynes: Synthesis of (E)-1,2-divinyldiethynylethenes having donor and acceptor chromophores at the terminus of alkyne

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 1152-1155

  Pahadi, Nirmal K ^a   Camacho, Draxel H ^a   Nakamura, Itaru ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; CHROMOPHORES; DIMERIZATION; PALLADIUM; SILICON; SOLVENTS; SYNTHESIS (CHEMICAL);

(E)-1,2-DIVINYLDIETHYNYLETHENES; ACCEPTOR CHROMOPHORES; HOAC-CATALYZED DIMERIZATION; PALLADIUM-CATALYZED DIMERIZATION;

OLEFINS;

1,2 DIVINYLDIETHYNYLETHENE DERIVATIVE; ALKYNE; ETHYLENE; IODIDE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHROMATOPHORE; CONJUGATION; DESILYLATION; DIMERIZATION; SONOGASHIRA REACTION; SYNTHESIS;

EID: 32144452366     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052262v     Document Type: Article

References (50)

1. (a) Harper, P.; Wherrett, B. Nonlinear Optics; Academic Press: New York, 1997.
2. (b) Saleh, B. E. A.; Teich, M. C. Fundamentals of Photonics; Wiley: New York, 1991.
3. (c) Tour, J. M. Chem. Rev. 1996, 96, 527-553.
4. (d) Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350-1377.
5. Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413.
6. (a) Scott, L. T.; Cooney, M. J. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, Germany, 1995; p 321.
7. (b) Puddephatt, R. J. Chem. Commun. 1998, 1055.
8. (c) Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107.
9. (d) Youngs, W. J.; Tesseir, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153.
10. (e) de Meijere, A.; Kozhushkov, S. I. Top. Curr. Chem. 1999, 201, 1.
11. (f) Haley, M. M.; Park, J. J.; Brand, S. C. Top. Curr. Chem. 1999, 201, 81.
12. (g) Bunz, U. H. F. Top. Curr. Chem. 1999, 201, 131.
13. (h) Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
14. (i) Hopf, H. Classics in Hydrocarbon Chemistry; Wiley-VCH: Weinheim, Germany, 2000.
15. (j) Laskoski, M.; Roidl, G.; Smith, M. D.; Bunz, U. H. F. Angew. Chem., Int. Ed. 2001, 40, 1460.
16. (k) Nielsen, B. M.; Utesch, F. N.; Moonen, N. N. P.; Boudon, C.; Gisselbrecht, P. J.; Concilio, S.; Piotto, P. S.; Seiler, P.; Günter, P.; Gross, M.; Diederich, F. Chem.-Eur. J. 2002, 8, 3601.
17. (a) Tykwinski, R. R.; Diederich, F. Liebigs Ann. Rec. 1997, 649.
18. (b) Diederich, F. Chem. Commun. 2001, 219.
19. Gobbi, L.; Seiler, P.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1999, 38, 674.
20. (a) Martin, R. E.; Gubler, U.; Boudon, C.; Gramlich, V.; Bosshard, C.; Gisselbrecht, J. P.; Günter, P.; Gross, M.; Diederich, F. Chem.-Eur. J. 1997, 3, 1505.
21. (b) Spreiter, R.; Bosshard, C.; Knöpfle, G.; Günter. P.; Tykwinski, R. R.; Schreiber, M.; Diederich, F. J. Phys. Chem. B 1998, 102, 29.
22. (c) Tykwinski, R. R.; Gubler, U.; Martin, R. E.; Diederich, F.; Bosshard, C.; Günter, P. J. Phys. Chem. B 1998, 102, 4451.
23. (d) Meier, H. Angew. Chem. 1992, 104, 1425;
24. Angew. Chem., Int. Ed. Engl. 1992, 31, 1399.
25. (e) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. 1998, 110, 416;
26. Angew. Chem., Int. Ed. 1998, 37, 403.
27. (f) Das-Gupta, D. K. In Introduction to Molecular Electronics; Petty, M. C., Bryce, M. R., Bloor, D., Eds.; Edward Arnold: London, 1995; pp 47-71.
28. (a) Lamrani, M.; Hamasaki, R.; Mitsuishi, M.; Miyashita, T.; Yamamoto, Y. Chem. Commun. 2000, 1595.
29. (b) Hamasaki, R., Ito, M.; Lamrani, M.; Mitsuishi, M.; Miyashita, T.; Yamamoto, Y. J. Mater. Chem. 2003, 13, 21.
30. (c) Tsuboya, N.; Lamrani, M.; Hamasaki, R.; Ito, M.; Mitsuishi, M.; Miyashita, T.; Yamamoto, Y. J. Mater. Chem. 2002, 12, 2701 and references therein.
31. For more examples, see: (d) Cumpston, H. B.; Ananthavel, S. P.; Barlow, S.; Dyer, D. L.; Ehrlich, J. E.; Erskine, L. L.; Heikal, A. A.; Kuebler, S. M.; Lee, I.-Y. S.; McCord-Maughon, D.; Qin, J.; Rockel, H.; Rumi, M.; Wu, X.-L.; Marder, S. R.; Perry, J. W. Nature 1999, 398, 51.
32. (e) Albota, M.; Beljonne, D.; Brédas, J.-L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord-Maughon, D.; Perry, J. W.; Rockel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 289, 1653.
33. (f) Kogej, T.; Beljonne, D.; Meyers, F.; Perry, J. W.; Marder, S. R.; Brédas, J. L. Chem. Phys. Lett. 1998, 298, 1.
34. (g) Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L.; He, G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863.
35. (a) Livingston, R. C.; Cox, L. R.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. 2001, 40, 2334.
36. (b) Landor, P. D. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: New York, 1982; Vol. 1, p 229.
37. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984; p 114.
38. Van Loon, J.-D.; Seiler, P.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1187.
39. For a preliminary communication, see: Camacho, D. H.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 924-925.
40. For reviews, see: (a) Campbell, I. B. In The Sonogashira Cu-Pd-Catalyzed Alkyne Coupling Reaction. Organocopper Reagents; Taylor, R. J. K., Ed.; IRL Press: Oxford, U.K., 1994; pp 217-235.
41. (b) Sonogashira, K.; Takahashi, S. Yuki Gosei Kagaku Kyokaishi 1993, 51, 1053.
42. (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3, pp 521-549.
43. See the Supporting Information for details.
44. Camacho, D. H. Ph.D. Dissertation book.
45. o, was calculated using the MOPAC94 PM3 method.
46. A similar kind of explanation was also made by another researcher. For an example, see: Helv. Chim. Acta 1996, 79, 2249 and references therein.
47. R. R. Tykwinski et al. have mentioned that the major absorption of the periphenylated iso-polydiacetylene (iso-PDA) compound arises from the ene-yne-ene segments. For example, see: Zhao, Y.; Slepkov, A. D.; Akoto, C. O.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. Chem.-Eur. J. 2005, 11, 321-329.
48. Diederich, F.; Luca, G. Top. Curr. Chem. 1999, 201, 43.
49. It is well-known that the elongation of the alkyl chains in N,N-dialkylanilines can enhance their electron-donating ability. For example, see: Helv. Chim. Acta 2004, 87, 1132 and reference therein.
50. If the UV-vis absorptions of NLO materials overlap with (or are extended to the region of) the double frequency value, 532 nm (2 ω), of the wavelength of an irradiated laser (1064 nm, 1 ω), it means that the materials will be decomposed by the newly generated short-wavelength laser.