A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Using Nickel Boride (cat.)-Borohydride Exchange Resin in Methanol.
The radical addition reaction of alkyl iodides with alpha,beta-unsaturated esters, nitriles, and ketones proceeds in moderate to excellent yields (50-95%) using Ni(OAc)(2) (0.05-0.2 equiv)-BER (3-5 equiv) in methanol in 1-9 h at room temperature or at 65 degrees C. Nickel boride on borohydride exchange resin (BER) is a good alternative reagent to tributyltin hydride for the coupling of alkyl iodides with the electron deficient alkenes in methanol. Compared with tributyltin hydride method, this method has an advantage of simple workup, since nickel boride-BER can be removed readily by filtration.
Sim
Tae Bo
TB
Department of Chemistry, Sogang University, Seoul 121-742, Korea.
Choi
Jaesung
J
Joung
Meyoung Ju
MJ
Yoon
Nung Min
NM