Novel role of carbon dioxide as a selective agent in palladium-catalyzed cyclotrimerization of alkynes
Jin-Heng Li
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, College of Chemistry and Chemical Engineering, Hum Normal University, Changsha, Hunan 410081, China
Search for more papers by this authorYe-Xiang Xie
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, College of Chemistry and Chemical Engineering, Hum Normal University, Changsha, Hunan 410081, China
Search for more papers by this authorJin-Heng Li
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, College of Chemistry and Chemical Engineering, Hum Normal University, Changsha, Hunan 410081, China
Search for more papers by this authorYe-Xiang Xie
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, College of Chemistry and Chemical Engineering, Hum Normal University, Changsha, Hunan 410081, China
Search for more papers by this authorAbstract
Carbon dioxide was found as a selective agent to promote the palladium-catalyzed cyclotrimerization of alkynes in water. Both aryl and alkylacetylenes afforded the corresponding cyclotrimerization products regioselectively in high yields using PdCl2, CuCl2, and CO2 as the catalytic system. However, tert-butylacetylene bearing a bulky group gave a dimerization product. Mechanism of this reaction was also discussed.
References
- 1(a) Stocchi, I. M. Industrial Chemistry, Ellis Horwood, New York, 1990. (b) Inoue, S.; Yamazaki, N. Organic and Bioorganic Chemistry of Carbon Dioxide, Kodansha, Tokyo, Wiley, New York, 1982. (c) Halman, M. M. Chemical Fixution of Carbon Dioxide, CRC Press, Boca Raton, 1993. (d) Arakawa, H.; Aresta, M.; Armor, J. N.; Barteau, M. A.; Bechman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Dornen, K.; Dubois, D.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, D. W.; Kelller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E.; Marks, T. J.; Morokuma, K.; Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Sornojai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem Rev. 2001, 101, 953.
- 2For representative reviews, see: (a)
Jessop, P. G.;
Leitner, W.,
Chemical Synthesis Using Supercntical Fluids, Wiley-VCH, Weinheim,
1999.
10.1002/9783527613687 Google Scholar(b) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475. (c) Li, J.; Jia, L.; Jiang, H. Chin. J. Org. Chem. 2000, 20, 293 (in Chinese). (d) Oakes, R. S.; Clifford, A. A.; Rayner, C. M. J. Chem. Soc., Perkin Trans. I 2001, 917.
- 3(a)
Wittmann, K.;
Wisniewski, W.;
Mynott, R.;
Leitner, W.;
Kranemann C. L.;
Rische, T.;
Eilbracht, P.;
Kluwer, S.;
Emsting, J. M.;
Elsevier, C. J.
Chem Eur. J.
2001,
7, 4584 and references cited therein.
10.1002/1521-3765(20011105)7:21<4584::AID-CHEM4584>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar(b) Li, J.; Xie, Y.; Yin, D.; Jiang, H. Green Chem. 2002, 4, 424. (c) Li, J.; Xie, Y.; Ym, D. J. Org. Chem. 2003, 68, 9867.
- 4(a) Peyrot F.; Martin, M.-T.; Migault, J.; Ducrocq, C. Eur J. Org. Chem 2003, 172. (b) Li, J.; Xie, Y.; Yin, D. Green Chem. 2002, 4, 505. (c) Gabriele, B.; Salemo, G.; Costa, M.; Chiusoli, G. P. Chem. Commun. 1999, 1381 and references cited therein.
- 5
Tsuji, J.
Organic Synthesis with Palladium Compounds, Springer-Verlag, New York,
1980, 162.
10.1007/978-3-642-67475-4 Google Scholar
- 6 Schore, N. E. Chem. Rev. 1988, 88, 1081.
- 7
Schore, N. E.
In
Comprehensive Organic Synthesis,
Vol. 5,
Eds. B. M. Trost;
I. Fleming;
L. A. Paquatte
Pergamon: Elmsford, New York,
1991,
p. 1129.
10.1016/B978-0-08-052349-1.00148-7 Google Scholar
- 8
Grotijahn, D. B.
in
Comprehensive Organomet. Chemistry II,
Vol 12,
Eds. E. W. Abel;
F. G. A. Stone;
G. Willunson;
L. S. Hegedus,
Pergamon, Tarrytown, New York,
1995,
p. 741.
10.1016/B978-008046519-7.00126-X Google Scholar
- 9 Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232.
- 10 Sigmen, M. S.; Fatlanf A. W.; Eaton, B. E. J. Am Chem. Soc. 1998, 120, 5130 and references cited therein.
- 11 Yokota, T.; Sakurai, Y.; Sakaguchi, S.; Iskii, Y. Tetrahedron Lett. 1997, 38, 3923.
- 12 Li, J.; Jiang, H.; Chen, M. J. Org. Chem. 2001, 66, 3627 and references cited therein.
- 13 Li, J.; Jiang, H.; Feng, A.; Jia, L. J. Org. Chem 1999, 64, 5984.
- 14 Li, J.; Li, G.; Liang, H.; Chen, M. Tetrahedron Lett. 2001, 42, 6923.
- 15 Li, J.; Jiang, H.; Chen, M. Chin. J. Chem 2001, 19, 689.
- 16 The effect of NaHCO3 on the palladium-catalyzed cyclotrimerization was also examined: only 9% yield of 2a was isolated from la by using 2 equiv. of NaHCO3 instead of CO2.
- 17 Weast, R. C. Handbook of Chemistry and Physics, CRC Press, Cleveland, 1980, p. C-172.
- 18 Lyle, R. E.; Dewitt, E. J.; Nichols, N. M.; Cleland, W. J. Am Chem. Soc. 1953, 75, 5959.
- 19 Hopff, H.; Gati, A. Helv. Chim. Acta 1965, 48, 509.
- 20 Vollhardt, K. P. C.; Winn, L. S. Tetrahedron Lett. 1985, 26. 709.
