Iodobenzene Dichloride Mediated Sequential C-Cl Bond Formation: A Safe, Convenient and Efficient Method for the Direct alpha,alpha-Dichlorination of beta-Dicarbonyl Compounds

Various -keto esters, 1,3-diketones, and -oxo amides are directly converted into their corresponding ,-dichloro--keto esters, 2,2-dichloro-1,3-diketones, and ,-dichloro--oxo amides, respectively, in moderate to high yields, using iodobenzene dichloride in dichloromethane in the presence of 4 angstro...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 47; no. 6; pp. 777 - 782
Main Authors Duan, Xiyan, Zhou, Huiyun, Tian, Xinlei, Liu, Jianwei, Ma, Junying
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.03.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
hypervalent iodine
ACTIVATION
COMPLEXES
FLORFENICOL
ALPHA,ALPHA-DIHALOGENATION
ALCOHOLS
dichlorination
ALKENES
dicarbonyl compounds
C-Cl bond formation
POLYVALENT IODINE COMPOUNDS
CHEMISTRY
iodobenzene dichloride
CHLORINATION
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Summary:Various -keto esters, 1,3-diketones, and -oxo amides are directly converted into their corresponding ,-dichloro--keto esters, 2,2-dichloro-1,3-diketones, and ,-dichloro--oxo amides, respectively, in moderate to high yields, using iodobenzene dichloride in dichloromethane in the presence of 4 angstrom molecular sieves at room temperature. This process is postulated to proceed via the iodobenzene dichloride mediated sequential oxidative -chlorination of the -dicarbonyl substrates.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1379973