Transition-Metal Free, One Pot Synthesis of Selenoesters via Reaction of Alkyl Selenides and Acyl Chlorides

Herein, we report a new and efficient method for the synthesis of selenoesters by a direct coupling reaction of alkyl selenides with acyl chlorides in ethanol under transition metal-free conditions. This nucleophilic acyl substitution afforded selenoesters in good yields. Traditionally, synthesis of...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 12; no. 12
Main Authors Duarte, Juliana S., De Oliveira, Sandynara A., Da Silva, Emily C. O., De Jesus, Andreia P. V., Vasconcelos, Leonardo G., De Sousa Junior, Paulo T., Rafique, Jamal, Saba, Sumbal, Stein, Andre L.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.12.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
One-pot synthesis
ACID
LIQUID
EFFICIENT SYNTHESIS
ALDEHYDES
Selenoesters
CLEAVAGE
DISELENIDES
SELENOL ESTERS
RADICAL-BASED ROUTE
Sonogashira
Green chemistry
Selenium
SE-SE
BOND
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Summary:Herein, we report a new and efficient method for the synthesis of selenoesters by a direct coupling reaction of alkyl selenides with acyl chlorides in ethanol under transition metal-free conditions. This nucleophilic acyl substitution afforded selenoesters in good yields. Traditionally, synthesis of selenoesters involve the reaction of acyl chlorides with an organoselenium anions generated in situ through the reductive cleavage of previously prepared diselenides. Our one-pot approach avoids the pre-preparation of diselenides and operated in atom-economical and environmentally friendly conditions. The synthetic utility of these selenoesters was studied using Se-butyl benzoselenoate as substrate in a Sonogashira-type cross-coupling reaction.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300474