Carbon dioxide promoted palladium-catalyzed cyclotrimerization of alkynes in water

Synthetic Communications

Volumn 34, Issue 9, 2004, Pages 1737-1743

  Li, Jin Heng ^a   Xie, Ye Xiang ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

Alkynes; Carbon dioxide; Cyclotrimerization; Palladium catalyzed; Regioselectivity

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE; CARBON DIOXIDE; CHLORIDE; COPPER CHLORIDE; FUNCTIONAL GROUP; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TERT BUTYL ACETYLENE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CYCLOTRIMERIZATION; DIMERIZATION; POLYMERIZATION; STEREOCHEMISTRY;

EID: 2442672782     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120030761     Document Type: Article

References (17)

1. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: New York, 1980, 162.
2. Schore, N.E. Transition metal-mediated cycloaddition reactions of alkynes in organic synthesis. Chem. Rev. 1988, 88, 1081.
3. Schore, N.E. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Paquatte, L.A., Eds.; Pergamon: Elmsford, NY, 1991; Vol. 5, Chapter 7.3, 1129.
4. Grotijahn, D.B. Comprehensive Organometallic Chemistry II; Abel, E.W., Stone, F.G.A., Wilkinson, G., Hegedus, L.S., Eds.; Pergamon: Tarrytown, NY, 1995; Vol. 12, 741.
5. Gevorgyan, V.; Yamamoto, Y. Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes. J. Organometallic. Chem. 1999, 576, 232.
6. Sigmen, M.S.; Fatlant, A.W.; Eaton, B.E. Cobalt-catalyzed cyclotrimerization of alkynes in aqueous solution. J. Am. Chem. Soc. 1998, 120, 5130, and references cited therein.
7. Yokota, T.; Sakurai, Y.; Sakaguchi, S.; Ishii, Y. Cyclotrimerization of alkynes using a multicatalytic system, Pd(II)/chlorohydroquinone/NPMOV, under dioxygen. Tetrahedron Lett. 1997, 38, 3923.
8. 2-induced regiospecifical synthesis of benzene derivatives in the palladium-catalyzed cyclotrimerization of alkynes. J. Org. Chem. 2001, 66, 3627, and references cited therein.
9. Li, J.; Jiang, H.; Feng, A.; Jia, L. Novel stereospecific syntheses of 3-chloroacrylate esters via palladium-catalyzed dicarbonylation of terminal acetylenes. J. Org. Chem. 1999, 64, 5984.
10. 2O/dioxane. Tetrahedron Lett. 2001, 42, 6923.
11. Li, J.; Jiang, H.; Chen, M. Effect of solvent and acid-base on palladium (II)-catalyzed dicarbonylation of terminal acetylenes: a general and efficient synthesis of maleic diesters and maleic anhydrides. Chin. J. Chem. 2001, 19, 689.
12. 2 and alk-l-ynes. Chem. Commun. 1999, 1381.
13. 2. Chem. Commun. 2001, 2194, and references cited therein.
14. Abia, M.; Choi, J.C.; Sakakura, T. Halogen-free process for the conversion of carbon dioxide to urethanes by homogeneous catalysis. Chem. Commun. 2001, 2238, and references cited therein.
15. Jessop, P.G.; Leitner, W. Chemical Synthesis Using Supercritical Fluids; Wiley-VCH: Weinheim, 1999.
16. Li, J.; Jia, L.; Jiang, H. Transition metal-catalyzed organic reactions in supercritical carbon dioxide. Chinese J. Org. Chem. 2000, 20, 293.
17. Oakes, R.S.; Clifford, A.A.; Rayner, C.M. The use of supercritical fluids in synthetic organic chemistry. J. Chem. Soc. Perkin Trans. 1 2001, 917.