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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Gallo, Rafael D. C. [1] ; Ahmad, Anees [1] ; Metzker, Gustavo [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 4
Affiliation:
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 23, n. 67, p. 16980-16984, DEC 1 2017.
Web of Science Citations: 13
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. (AU)

FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
Grantee:Carlos Alberto Montanari
Support type: Research Projects - Thematic Grants