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

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...

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Veröffentlicht in:	Chemistry : a European journal 2017-12, Vol.23 (67), p.16980
Hauptverfasser:	Gallo, Rafael D C, Ahmad, Anees, Metzker, Gustavo, Burtoloso, Antonio C B
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Anions Chemistry Halides Halogenation Halogens Ketones
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creator	Gallo, Rafael D C Ahmad, Anees Metzker, Gustavo Burtoloso, Antonio C B
description	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.
doi_str_mv	10.1002/chem.201704609
format	Article
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subjects	Alkylation Anions Chemistry Halides Halogenation Halogens Ketones
title	[alpha],[alpha]-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones
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