Synthesis of (Z)-ß-halo &#945;,ß-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid.

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

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

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

Afiliação

da Silva VAF; 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.

Org Biomol Chem ; 17(3): 519-526, 2019 01 16.

Article em En | MEDLINE | ID: mdl-30569046

RESUMO

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)-ß-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Tipo de estudo: Guideline Idioma: En Revista: Org Biomol Chem Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Brasil País de publicação: Reino Unido

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