Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds

Tetrahedron Letters

Volumn 48, Issue 46, 2007, Pages 8246-8249

  Vasilevsky, Sergei F ^a   Krivenko, Olga L ^a   Alabugin, Igor V ^b  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

^b FLORIDA STATE UNIVERSITY   (United States)

Author keywords

3 Imidazoline nitroxyles; Aryl and hetarylacetylenes; Cross coupling; Oxidative coupling; Stable radicals

Indexed keywords

1 HYDROXY 4 [2 (4 IODOPHENYL)VINYL] 2,2,5,5 TETRAMETHYL 3 IMIDAZOLINE 3 OXIDE; ACETYLENE DERIVATIVE; ALKYNE; COPPER DERIVATIVE; FUNCTIONAL GROUP; IMIDAZOLINE DERIVATIVE; NITROXYL RADICAL; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMISTRY; CROSS COUPLING REACTION; ELECTRONICS; MOLECULAR INTERACTION; MOLECULAR STABILITY; OXIDATION; REACTION ANALYSIS; SONOGASHIRA REACTION;

EID: 35348913663     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.031     Document Type: Article

References (27)

1. Imidazoline Nitroxides; Volodarsky, L. B. Ed., CRC: Boca Raton, Florida, Synthesis and Properties, 1988; Vol. I, 222 pp and Applications, Vol. II, 160 pp.
2. Voldarsky L.B., Reznikov V.A., and Ovcharenko V.I. Synthetic Chemistry of Stable Nitroxides (1994), CRC, Boca Raton p 221
3. Sviridenko F.B., Stass D.V., Kobzeva T.V., Tretyakov E.V., Klyatskaya S.V., Mshvidobadze E.V., Vasilevsky S.F., and Molin Yu.N. J. Am. Chem. Soc. 126 (2004) 2807
4. Vasilevsky S.F., Klyatskaya S.V., Korovnikova O.L., Stass D.V., Amitina S.A., Grigor'ev I.A., and Elguero J. Tetrahedron Lett. 45 (2004) 7741
5. Vasilevsky V.F., Klyatskaya S.V., Korovnikova O.L., Stass D.V., Amitina S.A., Grigor'ev I.A., and Elguero J. Tetrahedron 62 (2005) 4591
6. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 50 (1975) 4467
7. Tour J.M. Chem. Rev. 96 (1996) 537
8. Martin R.E., and Diederich F. Angew. Chem., Int. Ed. 38 (1999) 1350
9. Batsanov A.S., Collings J.C., Fairlamb I.J.S., Holland J.P., Howard J.A.K., Lin Z., Marder T.B., Parsons A.C., Ward R.M., and Zhu J. J. Org. Chem. 70 (2005) 703
10. A recent example:. Yin W., Srirama Sarma P.V.V., Ma J., Han D., Chen J.L., and Cook J.M. Tetrahedron Lett. 46 (2005) 6363
11. Rossi R., Carpita A., and Bigelli C. Tetrahedron Lett. 26 (1985) 523
12. Chen C., Ai Z., Lin J., Hong X., and Xi C. Synlett (2006) 2454
13. Lei A., Srivastava M., and Zhang X. J. Org. Chem. 67 (2002) 1969
14. Liu Q., and Burton D.J. Tetrahedron Lett. 38 (1997) 4371
15. Li J.-H., Liang Y., and Zhang X.-D. Tetrahedron 61 (2005) 1903
16. Nguyen P., Yuan Z., Agocs L., Lesley G., and Marder T.B. Inorg. Chim. Acta 220 (1994) 289
17. Takahashi A., Endo T., and Nozoe S. Chem. Pharm. Bull. 40 (1992) 3181
18. Jung F., Burger A., and Biellmann J.F. Org. Lett. 5 (2003) 383
19. Klyatskaya S.V., Tretyakov E.V., and Vasilevsky S.F. Russ. Chem. Bull., Int. Ed. 51 (2002) 128
20. Stroh C., Mayor M., and von Hänish C. Tetrahedron Lett. 45 (2004) 9623
21. 3 to yield 0.02 g (67%) of product 4.
22. Chinchilla R., and Najera C. Chem. Rev. 107 (2007) 874
23. Okuro K., Furuune M., Enna M., Miura M., and Nomura M. J. Org. Chem. 58 (1993) 4716
24. Cassar L. J. Organomet. Chem. 93 (1975) 259
25. Tretyakov E.V., Knight D.W., and Vasilevsky S.F. J. Chem. Soc., Perkin Trans. 1 (1999) 3713
26. 3 (elution with chloroform). Subsequent recrystallization gave pure compounds 11a-c.
27. 13C) = 5.88 G.