Details

Autor(en) / Beteiligte

• 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

Titel

Synthesis of (Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acidElectronic supplementary information (ESI) available. CCDC 1843637. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ob02110d

Erscheinungsjahr

2019-01

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 BF 3 (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. A procedure for the stereoselective synthesis of β-halovinyl derivatives via a conjugate addition of HX to ynones has been developed.