A novel approach towards the preparation of functionalized alkyne derivatives via ArS-mediated AdE reaction of cobaltcarbonyl complexed conjugated enynes

Tetrahedron

Volumn 66, Issue 12, 2010, Pages 2156-2161

  Tumanov, Vasily V ^a   Zatonsky, Georgy V ^a   Smit, William A ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; COBALT DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; PRIORITY JOURNAL;

EID: 76749155444     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.060     Document Type: Article

References (24)

1. Nicholas K.M. Acc. Chem. Res. 20 (1987) 207
2. Mueller T.J.J. Eur. J. Org. Chem. (2001) 2021
3. Schreiber S.L., Klimas M.T., and Sammakia T. J. Am. Chem. Soc. 109 (1987) 5749
4. Mikaelyan G.S., Gybin A.S., and Smit W.A. Izv. Akad. Nauk USSR (1985) 2277
5. Gybin A.S., Smit W.A., Caple R., Veretenov A.L., Shashkov A.S., Vorontsova L.G., Kurella M.G., Chertkov V.S., Karapetyan A.A., Kosnikov A.Y., Alexanyan M.S., Lindeman S.V., Panov V.N., Maleev A.V., Struchkov Y.T., and Sharpe S.M. J. Am. Chem. Soc. 114 (1992) 5555
6. Mayr H., Kuhn O., Schlierf C., and Ofial A.R. Tetrahedron 56 (2000) 4219
7. Tumanov V.V., and Smit W.A. Phosphorus, Sulfur Silicon Relat. Elem. 180 (2005) 1279
8. Mayr H., Bug T., Gotta M.F., Hering N., Irrgang B., Janker B., Kempf B., Loos R., Ofial A.R., Remennikov G., and Schimmel H. J. Am. Chem. Soc. 123 (2001) 9500
9. 2O catalyst (prepared according to. Mayr H., and Striepe W. J. Org. Chem. 50 (1985) 2995 ), in contrast to the rest of the Lewis acids, could be used in catalytic amounts (10-15 mol %.). However, its use in the reactions with isopropenylacetylenic complex 1b turned out to be inefficient due to the formation of voluminous precipitate, which was insoluble at low temperature (up to -30 °C). The attempts to run the reaction at higher temperature failed
10. Smit W.A., Caple R., and Smolyakova I.P. Chem. Rev. 94 (1994) 2359
11. Varghese, V.; Saha, M.; Nicholas, K. M. Org. Synth., CV 8, 460.
12. Vizniovsky C.S., Green J.R., Breen T.L., and Dalacu A.V. J. Org. Chem. 60 (1995) 7496
13. At present it is premature to discuss the details of the mechanism and the stereoselectivity pattern of the reaction, especially in view of the observed dependence of the syn/anti ratio on the nature of the Lewis acid (see Table 2).
14. Blanco-Urgoiti J., Añorbe L., Pérez-Serrano L., Domínguez G., and Pérez-Castells J. Chem. Soc. Rev. 33 (2004) 32
15. Sokolov D.V., Litvinenko G.S., and Isin Zh.I. Izv. Akad. Nauk Kaz. SSR, Ser. Khim. 2 (1959) 68
16. Schegolev A.A., Smit W.A., Mikaelyan G.S., Gybin A.S., YuKalyan B., Krimer M.Z., and Caple R. Izv. Akad. Nauk SSSR, Ser. Khim. (1984) 2571
17. [. Bull. Acad. Sci., USSR, Div. Chem. 33 (1984) 2355 (Engl. Transl)]
18. Harpp D.N., Friedlander B.T., and Smith R.A. Synthesis 3 (1979) 181
19. Ainsworth C., Chen F., and Kuo Y.N. J. Organomet. Chem. 46 (1972) 59
20. Cazeau P., Duboudin F., Moulines F., Babot Os., and Dunogues J. Tetrahedron 43 (1987) 2075
21. Hagen G., and Mayr H. J. Am. Chem. Soc. 113 (1991) 4954
22. Klusener P.A.A., Kulik W., and Brandsma L. J. Org. Chem. 52 (1987) 5261
23. Klusener P.A.A., Hommes H.H., Verkruijsse H.D., and Brandsma L. J. Chem. Soc., Chem. Commun. (1985) 1677
24. It is also to be emphasized that the described work-up procedure was found to be instrumental in order to obtain reproducibly good yields of the products (even on the multi-gram scale). Otherwise a substantial decomposition may occur obviously due to instability of the crude reaction products.