α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones

Chemistry : a European Journal
Rafael D C GalloAntonio C B Burtoloso

Abstract

A one-pot alkylation-halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem-difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem-dihalogenated ketones containing a combination of the same or two different halogens. Kinetic isotopic effects as well as reaction kinetic experiments give insight to the mechanism of these reactions.

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Citations

Sep 29, 2018·Angewandte Chemie·James D NeuhausNuno Maulide
Oct 6, 2018·Angewandte Chemie·Maximilian A GaniekPaul Knochel
Oct 22, 2020·Organic & Biomolecular Chemistry·Giorgiana Denisa BisagLuca Bernardi
Jan 31, 2018·Journal of the American Chemical Society·Carmelo E IaconoGraham Pattison
Aug 24, 2021·The Journal of Organic Chemistry·David Philip DayAntonio Carlos Bender Burtoloso
Dec 7, 2019·The Journal of Organic Chemistry·Christopher JanotChristophe Aïssa

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