Solvent-free synthesis of 2-pyrones from alkynes and carbon dioxide catalyzed by Ni(1,5-cyclooctadiene)2/trialkylphosphine catalysts

Synlett

Volumn , Issue 14, 2005, Pages 2141-2146

  Kishimoto, Yasuhisa ^a   Mitani, Ikuko ^b  

^a The General Environmental Technos Co Ltd   (Japan)

^b KANSAI ELECTRIC POWER CO   (Japan)

Author keywords

2 pyrone derivatives; Alkynes; Carbon dioxide; Ni(0) complex; Solvent free

Indexed keywords

2 PYRONE DERIVATIVE; ALKYNE DERIVATIVE; CARBON DIOXIDE; NICKEL (1,5 CYCLOOCTADIENE); NICKEL COMPLEX; PHOSPHINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLOADDITION; QUANTUM YIELD; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 24744457936     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872266     Document Type: Article

References (28)

1. (a) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329.
2. (b) Walther, D.; Schönberg, H.; Dinjus, E.; Sieler, J. J. Organomet. Chem. 1987, 334, 377.
3. (c) Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 3140.
4. (d) Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2002, 124, 15188.
5. For a discussion of the chemistry of 2-pyrone, see: Stauton, J. In Comprehensive Organic Chemistry, Vol. 4; Samnes, P. G., Ed.; Pergamon Press: Oxford, 1979, 629.
6. (a) Kvita, V.; Fischer, W. Chimia 1992, 46, 457.
7. (b) Kvita, V.; Fischer, W. Chimia 1993, 47, 3.
8. For a synthesized 2-pyrone with anti-HIV activity, see: Vara Prasad, J. V. N.; Para, K. S.; Lunney, E. A.; Ortwine, D. F.; Dunbar, J. B. Jr.; Ferguson, D.; Tummino, P. J.; Hupe, D.; Tait, B. D.; Domagala, J. M.; Humblet, C.; Bhat, T. N.; Liu, B.; Guerin, D. M. A.; Baldwin, E. T.; Erickson, J. W.; Sawyer, T. K. J. Am. Chem. Soc. 1994, 116, 6989.
9. Benign by Design. Alternative Synthetic Design for Pollution Prevention, Vol. 577; Anastas, P. T.; Farris, C. A., Eds.; American Chemical Society: Washington DC, 1994.
10. Eckert, C. A.; Knutson, B. L.; Debenedetti, P. G. Nature (London, U.K.) 1996, 383, 313.
11. Chemical Synthesis Using Supercritical Fluids; Jessop, P. G.; Leitner, W., Eds.; Wiley-VCH: Weinheim, 1999.
12. Reetz, M. T.; Konen, W.; Strack, T. Chimia 1993, 47, 493.
13. 2 and catalyst both dissolved in liquid 3-hexyne) and not in ScCO2: Dinjus, E. COST/Dechema Workshop; Lahnstein Germany, April 1995.
14. Kreher, U.; Schebesta, S.; Walther, D. Z. Anorg. Allg. Chem. 1998, 624, 602.
15. 1H NMR spectrum was identical to the spectral data reported in ref. 1a.
16. CAUTION: Certain alkynes turn immediately brown when they are mixed with trialkylphosphines and the use of such alkynes does not give desired results. The reason for this is unclear at this time, but we recommend the use of the alkynes that cause no color change.
17. The product yield was determined by GC analysis on the basis of the alkyne 1 employed. Thus, the yield (%) of 2-pyrone 2 = .100 × [(mmol of alkyne component in 2)/(mmol of 1)] = 100 × [(2 × mmol of 2)/(mmol of 1)]; and the yield (%) of alkyne trimer 4 or 5 = 100 × [(mmol of alkyne component in 4 or 5)/(mmol of 1)] = 100 × [(3 × mmol of 4 or 5)/(mmol of 1)]. The selectivity for 2 is defined as the mol% of 2 in all of the reaction products and is calculated from the yields of 2, 4, and 5 by using the above equations. Thus, the selectivity (%) for 2 = 100 × [(mmol of 2)/(mmol of 2 + mmol of 4 + mmol of 5)] = 100 × [(% yield of 2)/2]/{[(% yield of 2)/2] + [(% yield of 4)/3] + [(% yield of 5)/3]}.
18. 3, see: (a) Sigma-Aldrich Library of Chemical Safety Data, Vol. 2; Lenga, R. E., Ed.; Sigma-Aldrich Corp.: Milwaukee, 1995, 3435C.
19. (b) Sigma-Aldrich Library of Regulatory & Safety Data, Vol. 1; Lenga, R. E.; Votoupal, K. L., Eds.; Sigma-Aldrich Corp.: Milwaukee, 1993, 1087E.
20. 3, see: Sigma-Aldrich Library of Regulatory & Safety Data, Vol. 1; Lenga, R. E.; Votoupal, K. L., Eds.; Sigma-Aldrich Corp.: Milwaukee, 1993, 1087C.
21. 2: 320.2715. Found: 320.2729.
22. 2: 180.1146. Found: 180.1144.
23. 6: 272.1260. Found: 272.1257.
24. + - 32], 295 (100), 265 (42), 233 (30), 203 (23).
25. (a) Walther, D.; Bräunlich, G.; Kempe, R.; Sieler, J. J. Organomet. Chem. 1992, 436, 109.
26. (b) Hoberg, H.; Schaefer, D.; Burkhardt, G.; Kruger, C.; Romao, M. J. Organomet. Chem. 1984, 266, 203.
27. Bartik, T.; Himmler, T.; Schulte, H.-G.; Seevogel, K. J. Organomet. Chem. 1984, 272, 29.
28. Bodner, G. M.; May, M. P.; McKinney, L. E. Inorg. Chem. 1980, 19, 1951.