Selectfluor and TBAX (Cl, Br) Mediated Oxidative Chlorination and Bromination of Olefins
Ziya Dağalan, Ramazan Koçak*, Arif Daştan and Bilal Nişancı*
*Department of Chemistry, Faculty of Sciences, Ataturk
University, Erzurum 25240, Turkey, Email: ramazan.kocak
atauni.edu.tr,
bnisanciatauni.edu.tr
Z. Dağalan, R. Koçak, A. Daştan, B. Nişancı, Org. Lett., 2022, 24, 8261-8264.
DOI: 10.1021/acs.orglett.2c02627
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Abstract
The use of Selectfluor as an oxidant and tetrabutylammonium bromide/chloride salts as a halogen source enables a metal-free and molecular halogen reagent-free dihomohalogenation methodology. This effective strategy provides various fluorine-free halogenated products easily in quantitative yields from alkenes, alkynes, and natural products.
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General procedure for Chlorination
Olefin (0,5 mmol), Selectfluor (209 mg, 0,6 mmol) and TBAC (333 mg, 1.2 mmol) were dissolved in 2 mL CH3CN in an ACE pressure tube. The reaction mixture was stirred at 100°C for 2 hours. The mixture was cooled to RT and the solvent was evaporated under reduced pressure. The crude reaction mixture was purified by column chromatography on silica gel (n-hexane/EtOAc (9:1)).
General procedure for Bromination
Olefin (0,5 mmol), Selectfluor (218 mg, 0,6 mmol) and TBAB (386 mg, 1.2 mmol) were dissolved in 2 mL CH3CN in an ACE pressure tube. The reaction mixture was stirred at room temperature for 5 minutes. The mixture was cooled to RT and the solvent was evaporated under reduced pressure. The crude reaction mixture was purified by column chromatography on silica gel (n-hexane/EtOAc (9:1)).
Key Words
dibromination, dichlorination, Selectfluor
ID: J54-Y2022
