Michael-type reaction of ethyl bromodifluoroacetate with alpha,beta- unsaturated carbonyl compounds in the presence of copper powder.
We have reported that the reaction of ethyl bromodifluoroacetate (1) with alkenyl iodides in the presence of copper powder gives ethyl alkenyldifluoroacetates. As an extension of this reaction, reaction of 1 with Michael acceptors in the presence of copper powder was examined and found to give 1,4-addition products selectively, unless the acceptor has a group stabilizing a radical intermediate, such as a phenyl group.
Sato
K
K
Faculty of Pharmaceutical Sciences, Setsunan University, Hirakata, Osaka, Japan.
Tamura
M
M
Tamoto
K
K
Omote
M
M
Ando
A
A
Kumadaki
I
I
D003300:Copper / Q000737:chemistry*; D005463:Fluoroacetates / Q000737:chemistry*
D005463:Fluoroacetates; D003300:Copper