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

Org Biomol Chem. 2019 Jan 16;17(3):519-526. doi: 10.1039/c8ob02110d.

Authors

Vitor A F da Silva¹, Gustavo P da Silva, Bianca T Matsuo, Akbar Ali, Rebecca L Davis, Julio Zukerman-Schpector, Arlene G Corrêa, Márcio W Paixão

Affiliation

¹ Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, São Paulo, Brazil. mwpaixao@ufscar.br.

PMID: 30569046
DOI: 10.1039/c8ob02110d

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.