Ruthenium-catalyzed coupling of unactivated olefins with unactivated alkynes

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7361-7364

  Murakami, Masahiro ^a   Ubukata, Minoru ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkenes; Alkynes; Dienes; Ruthenium and compounds

Indexed keywords

ALKADIENE; ALKENE; ALKYNE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; JAPAN; MOLECULAR INTERACTION;

EID: 0032190832     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01580-9     Document Type: Article

References (17)

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8. 8 When two equivalents of 1-octene to phenylacetylene were used, the yield of 2 decreased to 26% and an increase in the acetylene dimer (1,4-diphenylbut-1-en-3-yne, 40%) was observed.
9. 22: C, 89.65; H, 10.35. Found: C, 89.80; H, 10.35.
10. 10 A stoichiometric reaction of a ruthenium complex that couples a ligand olefin to a terminal alkyne was reported during the course of the present investigation. An analogous mechanism was proposed therein: C. Slugovc, K. Mereiter, R. Schmid, and K. Kirchner, J. Am. Chem. Soc., 120, 6175 (1998).
11. 6 as the catalyst afforded a similar result.
12. 2Cl] and phenylacetylene under similar conditions has been reported: M. I. Bruce, C. Hameister, A. G. Swincer, and R. C. Wallis, Inorg. Synth., 21, 78 (1982).
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14. 14 For recent examples of the synthesis of 1,3-dienes, see: a) R. Stragies, M. Schuster, and S. Blechert, Angew. Chem., Int. Ed. Engl., 36, 2518 (1997);
15. b) A. Kinoshita, N. Sakakibara, and M. Mori, J. Am. Chem. Soc., 119, 12388 (1997).
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17. b) C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996) and references therein.