Coupling of butyl vinyl tellurides with metal acetylides catalyzed by nickel complexes

Tetrahedron Letters

Volumn 45, Issue 25, 2004, Pages 4927-4930

  Raminelli, Cristiano ^a   Gargalaka Jr , João ^a   Silveira, Cláudio C ^b   Comasseto, João V ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Coupling reaction; Nickel complexes catalysis; Z Butyl vinyl tellurides

Indexed keywords

ACETIC ACID DERIVATIVE; METAL; NICKEL COMPLEX; TELLURIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 2942516522     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.120     Document Type: Article

References (13)

1. For leading references see: Barros S.M., Comasseto J.V., Berriel J.N. Tetrahedron Lett. 30:1989;7353
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3. Tucci F.C., Chieffi A., Comasseto J.V., Marino J.P. J. Org. Chem. 1996;4975
4. For recent reviews see: Comasseto J.V., Barrientos-Astigarraga R.E. Aldrichim. Acta. 33:2000;66
5. Vieira M.L., Zinn F.K., Comasseto J.V. J. Braz. Chem. Soc. 12:2001;586
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7. Zeni G., Comasseto J.V. Tetrahedron Lett. 40:1999;4619
8. For a review see: Zeni G., Braga A.L., Stefani H.A. Acc. Chem. Res. 36:2003;731
9. Komiya S. Komiya S. Synthesis of Organometallic Compounds - A Practical Guide. Vol. 1:1997;249 John Wiley and Sons, Chichester
10. Silveira C.C., Braga A.L., Vieira A.S., Zeni G. J. Org. Chem. 68:2003;662
11. Renson M. Patai S., Rappoport Z. The Chemistry of Organic Selenium and Tellurium Compounds. Vol. 1:1986;399 John Wiley and Sons, Chichester
12. Typical procedure for the preparation of lithium alkynoates: preparation of 1-heptynyl lithium: To a 50 mL two-necked round-bottomed flask under nitrogen atmosphere were added THF (10 mL) and 1-heptyne (11 mmol, 1.10 g, 1.5 mL). Then n-BuLi (7.7 mL; 10 mmol of a 1.3 M solution in hexane) was added dropwise at - 70°C. The mixture was stirred for 10 min. After this time the solution of 1-heptynyl lithium is ready for use.
13. 1H NMR spectrum. A GC analysis of the purified product showed that it was constituted by a 95:5 mixture of the E and Z isomers of 4j, respectively