Iridium-catalyzed addition of acid chlorides to terminal alkynes.
An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes to afford (Z)-beta-chloro-alpha,beta-unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr) was changed to a phosphine (RuPhos), the addition occurred with decarbonylation to give the corresponding (Z)-vinyl chlorides. Furthermore, the former reaction using IrCl(cod)(IPr) can be applied to the catalytic synthesis of 2,5-disubstituted furans.
Iwai
Tomohiro
T
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Fujihara
Tetsuaki
T
Terao
Jun
J
Tsuji
Yasushi
Y