1,4-Addition reaction of ethyl bromodifluoroacetate to Michael acceptors in the presence of copper powder: Improvement of the reaction using TMEDA as an additive

Graphic Reaction of ethyl bromodifluoroacetate with a variety of Michael acceptors was tremendously improved by the addition of TMEDA. Using this additive, 1,4-adducts were formed exclusively, and any 1,2-adducts or radical adducts were not obtained. THF or other low boiling solvents can be used as...

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Published inJournal of fluorine chemistry Vol. 121; no. 1; pp. 105 - 107
Main Authors Sato, Kazuyuki, Nakazato, Sumika, Enko, Hiroko, Tsujita, Hiroaki, Fujita, Katsumi, Yamamoto, Takeya, Omote, Masaaki, Ando, Akira, Kumadaki, Itsumaro
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 01.05.2003
Elsevier
Subjects
1,4-Addition
Bromodifluoroacetate
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Fluorine
Organocopper reagent
Physical Sciences
Science & Technology
TMEDA
Organocopper reagent
TMEDA
Fluorine
Bromodifluoroacetate
1,4-Addition
bromodifluoroacetate
1,4-addition
SILYL ACETAL
fluorine
organocopper reagent
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Summary:Graphic Reaction of ethyl bromodifluoroacetate with a variety of Michael acceptors was tremendously improved by the addition of TMEDA. Using this additive, 1,4-adducts were formed exclusively, and any 1,2-adducts or radical adducts were not obtained. THF or other low boiling solvents can be used as a solvent. This simplifies the work-up of the reaction effectively.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(03)00003-4