A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity

α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus all...

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Bibliographic Details
Published inTetrahedron Vol. 72; no. 3; pp. 420 - 430
Main Authors Munyemana, François, George, Isabelle, Devos, Alain, Colens, Alain, Badarau, Eduard, Frisque-Hesbain, Anne-Marie, Loudet, Aurore, Differding, Edmond, Damien, Jean-Marie, Rémion, Jeanine, Van Uytbergen, Jacqueline, Ghosez, Léon
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.01.2016
Elsevier
Subjects
Acyl halides
Alcohols
Alkyl halides
Carboxylic acids
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
α-Haloenamines
Acyl halides
Carboxylic acids
Alkyl halides
α-Haloenamines
Alcohols
HALIDES
alpha-Haloenamines
ALKYL
ENAMINES
NEUTRAL CONDITIONS
SELECTIVE CONVERSION
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Summary:α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.11.060