Pd-Ag catalyzed selective dicoupling of α-trialkylsilyl α,ω-diynes; the first one-pot synthesis of dienediynes

Journal of Organometallic Chemistry

Volumn 687, Issue 2, 2003, Pages 420-424

  Halbes Létinois, Ulla ^a   Pale, Patrick ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Acetylenes; Coupling reactions; Dienediynes; Palladium; Silver; Vinyl triflates

Indexed keywords

ALKADIENE; DIENEDIYNE DERIVATIVE; N,N DIMETHYLFORMAMIDE; PALLADIUM; SILVER; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; REACTION ANALYSIS; ROOM TEMPERATURE; SEQUENTIAL ANALYSIS; SYNTHESIS;

EID: 0344443270     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2003.07.003     Document Type: Article

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26. Readily obtained by treatment of dimedone with triflic anhydride in the presence of base.
27. The TBS group was used for convenience during the synthesis of 6. As demonstrated earlier [10b], it does not affect the reactivity during the coupling step.
28. The diyne 6 was conveniently obtained from the commercially available 3-methylbut-1-yn-3-ol through the following sequence: Bromination then malonate displacement followed by decarboxylation and reduction provided 3,3-dimethylpent-4-ynol. Silylation then oxidation and ethynyl bromomagnesium addition yielded 6.