The synthesis of vinyl naphthalenes with fluorinated side chains

Kazennikova, G. V.; Talalaeva, T. V.; Zimin, A. V.; Simonov, A. P.; Kocheshkov, K. A.

doi:10.1007/bf00905944

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“…The isolated yield of 16 was 71%. 1-Iodonaphthalene coupled with the trifluoroethenylzinc reagent under normal coupling reaction conditions to produce the corresponding styrene 17 in 83% isolated yield . The heterocyclic iodide, 2-iodothiophene, reacted with the trifluoroethenylzinc reagent within 1 h under normal coupling reaction conditions to produce a mixture of products from which the product styrene 18 was isolated in 59% yield 13a…”

Section: Resultsmentioning

confidence: 99%

Room Temperature Preparation of Trifluoroethenylzinc Reagent by Metalation of the Readily Available Halocarbon HFC-134a and an Efficient, Economically Viable Synthesis of 1,2,2-Trifluorostyrenes

Raghavanpillai

Burton

2004

J. Org. Chem.

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Trifluoroethenylzinc reagent [CF(2)=CFZnX] was generated from the readily available halocarbon HFC-134a by an in situ metalation-transmetalation procedure at temperatures near to room temperature (15-20 degrees C). By systematic standardization of the metalation experiments by manipulation of solvent, cosolvent, temperature, zinc salt, and the base, the trifluoroethenylzinc reagent was produced in 73% yield at 20 degrees C in THF medium. The palladium-catalyzed cross-coupling reaction of the trifluoroethenylzinc reagent with various aryl iodides was carried out under mild reaction conditions to produce 1,2,2-trifluorostyrenes in 59-86% isolated yields. The stability of the intermediate trifluoroethenyllithium reagent was compared at different temperatures and solvent systems. Experimental evidence for the mono-anion from HFC-134a (CF(3)CHF(-)) was obtained by the trapping of the mono-anion with zinc halide in THF/TMEDA medium. The structure and complexation of both the mono- and bis-trifluoroethenylzinc reagents with TMEDA and other ligands are discussed.

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Section: Resultsmentioning

confidence: 99%