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Issue 3, 2019
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Synthesis of (Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid

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Abstract

A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (Brønsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)-β-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.

Graphical abstract: Synthesis of (Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid

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Publication details

The article was received on 28 Aug 2018, accepted on 11 Dec 2018 and first published on 11 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02110D
Citation: Org. Biomol. Chem., 2019,17, 519-526

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    Synthesis of (Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid

    V. A. F. da Silva, G. P. da Silva, B. T. Matsuo, A. Ali, R. L. Davis, J. Zukerman-Schpector, A. G. Corrêa and M. W. Paixão, Org. Biomol. Chem., 2019, 17, 519
    DOI: 10.1039/C8OB02110D

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