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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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,^ab Rebecca L. Davis,

*^c Julio Zukerman-Schpector,^a Arlene G. Corrêa

^a and Márcio W. Paixão

*^a

Author affiliations

* Corresponding authors

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

^b Department of Chemistry, University of Sargodha, Pakistan

^c Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, 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

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C8OB02110D
Article type: Paper
Submitted: 28 Aug 2018
Accepted: 11 Dec 2018
First published: 11 Dec 2018

Download Citation

Org. Biomol. Chem., 2019,17, 519-526

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements