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

Vitor A. F. da Silva; Gustavo P. da Silva; Bianca T. Matsuo; Akbar Ali; Rebecca L. Davis; Julio Zukerman-Schpector; Arlene G. Corrêa; Márcio W. Paixão

doi:10.1039/C8OB02110D

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

Vitor A. F. da Silva,^a Gustavo P. da Silva,^a Bianca T. Matsuo,^a Akbar Ali,^a^b Rebecca L. Davis,*^c Julio Zukerman-Schpector,^a Arlene G. Corrêa^a and Márcio W. Paixão*^a

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* Corresponding authors

^a Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos – UFSCar, São Carlos, Brazil
E-mail: mwpaixao@ufscar.br

^b Department of Chemistry, University of Sargodha, Pakistan

^c Department of Chemistry, University of Manitoba, Winnipeg, Canada
E-mail: rebecca.davis@umanitoba.ca

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.

This article is part of the themed collections: Synthetic methodology in OBC and Catalysis & biocatalysis in OBC

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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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Vitor A. F. da Silva

Gustavo P. da Silva

Bianca T. Matsuo

Akbar Ali

Rebecca L. Davis

Julio Zukerman-Schpector

Arlene G. Corrêa

Márcio W. Paixão

Organic & Biomolecular Chemistry

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

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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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