A Phthalimide Derivative for Selective Iodination of Acrylic Esters
N-iodophthalimide [I1052] is utilized in the selective iodination at the α-position of acrylic esters. When acrylic esters react with I1052 in the presence of a catalytic amount of 3-quinuclidinol and KF-Celite under light-shielded conditions, the iodination proceeds via a Morita-Baylis-Hillman type reaction to give α-iodoacrylic esters in good yields. This reaction proceeds only with acrylic esters and not with α,β-unsaturated esters bearing a substituent at the β-position. Given products can be applied in cross couplings such as the Nozaki-Hiyama-Kishi reaction.
Pentafluoroethylation Using Economical Ethyl Pentafluoropropionate
Ethyl pentafluoropropionate [P1123] is used as a source of pentafluoroethyl moiety. When P1123 is added to a mixture of copper(I) chloride and potassium tert-butoxide, the pentafluoroethyl cuprate intermediate is formed in situ. Upon addition of boronic acids or aryl bromides in air or under argon atmosphere, respectively, the cross coupling proceeds and the pentafluoroethyl moiety is introduced. One of the advantages of this reaction is that it is economical to insert the pentafluoroethyl moiety because of the use of inexpensive reagents.