Addition of α,α-Difluoroiodomethyl Ketones to Alkenes with a Copper Catalyst

Abstract

The addition reactions of <TEX>$\alpha$</TEX>,<TEX>$\alpha$</TEX>-difluoroiodomethyl n-butyl ketone, α,α-difluoroiodomethyl cyclohexyl ketone, or <TEX>$\alpha$</TEX>,<TEX>$\alpha$</TEX>-difluoroiodomethyl phenyl ketone to alkenes were successfully accomplished in good yields in the presence of copper powder. The reaction was also applicable to alkenes containing a variety of functional groups such as ester, trimethylsilyl, or ether group. Acetonitrile was determined to be the best solvent in the present study and the reaction was performed at 55 <TEX>${^{\circ}C}$</TEX> for 15-22 h. This reaction provides a new, efficient and general method for the synthesis of <TEX>$\alpha$</TEX>,<TEX>$\alpha$</TEX>-difluoro functionalized ketones.