Reductive Hydrodehalogenation of Halogenated Carboxylic Acid Derivatives Using a DMSO/HCOONa(.)2H(2)O System

A practical and operationally simple hydrodehalogenation of halogenated carboxylic acid derivatives using a DMSO/ HCOONa center dot 2H(2)O system is developed. This protocol avoids the involvement of light irradiation, electrochemical apparatus, transition metals, radical initiators, strong bases, a...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 15; pp. 2691 - 2695
Main Authors Liu, Guyue, Hao, Feiyue, Liang, Lingling, Jin, Zhengneng, Wu, Jiashou
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 21.04.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
CYCLIZATION REACTION
ELECTRON-TRANSFER
HYDROGENATION
SODIUM HYDRIDE
DEUTERATION
ARYL HALIDES
CHLORIDES
FACILE
ALPHA-KETO AMIDES
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Summary:A practical and operationally simple hydrodehalogenation of halogenated carboxylic acid derivatives using a DMSO/ HCOONa center dot 2H(2)O system is developed. This protocol avoids the involvement of light irradiation, electrochemical apparatus, transition metals, radical initiators, strong bases, and other additional additives. Control experiments suggest that HCOONa might function as a hydride donor in the reduction process via nucleophilic substitution or addition to achieve the hydrodehalogenation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00782