Stable but reactive perfluoroalkylzinc reagents: application in ligand-free copper-catalyzed perfluoroalkylation of aryl iodides.
The aromatic perfluoroalkylation catalyzed by a copper(I) salt with bis(perfluoroalkyl)zinc reagents Zn(RF)2(DMPU)2, which were prepared and then isolated as a stable white powder from perfluoroalkyl iodide and diethylzinc, was accomplished to provide the perfluoroalkylated products in good-to-excellent yields. The advantages of this reliable and practical catalytic reaction are 1) air-stable and easy-to-handle bis(perfluoroalkyl)zinc reagents can be utilized, 2) the reagent is reactive and hence the operation without activators and ligands is simple, and 3) not only trifluoromethylation but also perfluoroalkylation can be attained.
Department of Applied Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2776.
Kohsuke
K
Aikawa
Yuzo
Y
Nakamura
Yuki
Y
Yokota
Wataru
W
Toya
Koichi
K
Mikami
copper; perfluoroalkylation; perfluoroalkylzinc; synthetic methods; transmetallation