Heterogeneously catalyzed efficient alkyne-alkyne homocoupling by supported copper hydroxide on titanium oxide

Chemistry - A European Journal

Volumn 15, Issue 31, 2009, Pages 7539-7542

  Oishi, Takamichi ^a   Katayama, Tatsuyori ^a   Yamaguchi, Kazuya ^a,b   Mizuno, Noritaka ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Alkynes; Copper; Heterogeneous catalysis; Homocoupling; Molecular oxygen

Indexed keywords

ALKYNES; ALKYNYL; BUTADIYNE; CATALYTIC ACTIVITY; COPPER HYDROXIDE; ETHYNYLBENZENE; HETEROGENEOUS CATALYSIS; HETEROGENEOUS CATALYST; HETEROGENOUS CATALYSTS; HOMOCOUPLING; HOMOCOUPLING REACTIONS; INDUCTIVELY COUPLED PLASMA ATOMIC EMISSION SPECTROSCOPY; OXYGEN ATMOSPHERE;

ACETYLENE; ATOMIC EMISSION SPECTROSCOPY; ATOMIC SPECTROSCOPY; BENZENE; CATALYSIS; CATALYSTS; COPPER; HYDROGEN; INDUCTIVELY COUPLED PLASMA; MOLECULAR OXYGEN; TITANIUM; TITANIUM OXIDES; TOLUENE;

COPPER OXIDES;

ALKYNE; ALKYNE DERIVATIVE; COPPER; COPPER HYDROXIDE; HYDROXIDE; TITANIUM; TITANIUM DIOXIDE;

ARTICLE; CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKYNES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; DIYNES; HYDROXIDES; OXIDATION-REDUCTION; TITANIUM;

EID: 67949089508     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901080     Document Type: Article

References (42)

1. F. Bohlmann. F. T. Burkhart, C. Zero, Naturally Occurring Acetylenes, Academic Press, London. 1973.
2. L. Hansen, P. M. Boll. Phytochemistry 1986. 25, 285.
3. H. Matsunaga. M. Kalano, H. Yamamoto, H. Fujito. M. Mori, K. Takata, Chem. Pharm. Bull. 1990, 38, 3480.
4. P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740;
5. Angew. Chem. Int. Ed. 2000, 39, 2632.
6. C. Glaser, Ber. Dtsch. Chem. Ges. 1869, 2, 422.
7. A. S. Hay, J. Org. Chem. 1962. 27. 3320.
8. I. D. Campbell, G. Eglinton, Org. Synth. 1965, 45, 39.
9. J. Li, H. Jiang, Chem. Commun. 1999. 2369.
10. R. Salazar. L. Fomina, S. Fomine, Polym. Bull. 2001, 47. 151.
11. A. Sharifi, M. Mirzaei, M. R. Naimi-Jamal, J. Chem. Res. 2002, 628.
12. J. S. Yadav, B. V. S. Reddy, K. B. Reddy, K. U. Gayathri, A. R. Prasad. Tetrahedron Lett. 2003, 44, 6493.
13. L. Wanga. J. Yana, P. Lia. M. Wanga, C. Su, J. Chem. Res. 2005,112.
14. X. Lu, Y. Zhang, C. Luo, Y. Wang. Synth. Commun. 2006, 36, 2503.
15. K. Kamata, S. Yamaguchi. M. Kotani. K. Yamaguchi, N. Mizuno, Angew. Chem. 2008, 120, 2441;
16. Angew. Chem. Int. Ed. 2008, 47, 2407.
17. K. Yamaguchi. K. Kamata, S. Yamaguchi, M. Kotani. N. Mizuno. J. Catal. 2008. 258. 121.
18. W. A. Herrmann, V. P. W. Böhm, C. V. K. Gstüttmayr, M. Grosche. C.-P. Reisinger. T. Weskamp. J. Organomet. Chem. 2001. 617-618. 616.
19. A. Lei, M. Srivastava, X. Zhang. J. Org. Chem. 2002, 67. 1969.
20. I. J. S. Fairlamb, P. S. Bäuerlein, L. R. Marrison, J. M. Dickinson, Chem. Commun. 2003, 632.
21. J. Li, Y. Liang. X.-D. Zhang. Tetrahedron 2005. 61. 1903.
22. J.-H. Li, Y. Liang. Y.-X. Xie. J. Org. Chem. 2005. 70, 4393.
23. S. M. Auer, M. Schneider. A. Baiker. J. Chem. Soc. Chem. Commun. 1995, 2057.
24. B. C. Zhu. X. Z. Jiang. Appl. Organomet. Chem. 2007. 21, 345.
25. P. Kuhn. A. Alix, M. Kumarraja, B. Louis. P. Pale. J. Sommer. Eur. J. Org. Chem. 2009, 423.
26. K. Yamaguchi. N. Mizuno, Angew. Chem. 2002, 114, 4720: Angew. Chem. Int. Ed. 2002. 41,4538.
27. K. Yamaguchi. N. Mizuno, Angew. Chem. 2003, 115. 1518:
28. Angew. Chem. Int. Ed. 2003. 42, 1480.
29. K. Yamaguchi. M. Matsushita, N. Mizuno. Angew. Chem. 2004. 116. 1602:
30. Angew. Chem. Int. Ed. 2004, 43,1576.
31. H. Fujiwara. Y. Ogasawara. K. Yamaguchi. N. Mizuno. Angew. Chem. 2007. 119, 5294:
32. Angew. Chem. Int. Ed. 2007, 46, 5202.
33. W. Kim, K. Yamaguchi. N. Mizuno. Angew. Chem. 2008, 120, 9389:
34. Angew. Chem. Int. Ed. 2008, 47, 9249.
35. K. Yamaguchi. T. Koike, J. W. Kim, Y. Ogasawara, N. Mizuno. Chem. Eur. J. 2008. 14. 11480.
36. Non-polar toluene and p-xylene were good solvents and gave quantitative yields of 2a for the homocoupling of la under the conditions described in Table 1. In contrast, polar protic as well as aprotic solvents such as 2-propanol. water. N.N-dimethylformamide, and dimethyl sulfoxide were poor likely because of their strong coordination to lhe aclive copper center.
37. 2 solution.
38. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485.
39. H. Irie, S. Miura. K. Kamiya, K. Hashimoto, Chem. Phys. Lett. 2008, 457, 202.
40. Purification of Laboratory Chemicals. 3rd ed. (Eds.: D.D. Perrin. W. L. F. Armarego), Pergamon Press, Oxford, 1988.
41. D. Briggs, M. P. Seah, Practical Surface Analysis by Auger and X-ray Photoelectron Spectroscopy, Wiley, New York. 1983.
42. G. P. Williams in CRC Handbook of Chemistry and Physics. 82nd ed. (Ed.: D. R. Lida). CRC Press, Washington 2001, Section 10, p. 200-205.