Fukuyama Reduction and Integrated Thioesterification/Fukuyama Reduction of Thioesters and Acyl Chlorides Using Continuous Flow.

Abstract

Fukuyama redn. of thioesters has been achieved using a polymer-supported Pd[0] catalyst (Pd/XAD-4), and continuous flow conditions. The generality of this reaction is good with a range of aldehydes prepd. in excellent yields. In addn., an integrated multistep thioesterification/Fukuyama redn. has been developed that allows acyl chlorides to be directly converted to the corresponding aldehydes. Integral to this process is the use of polymer-supported amine and isocyanate reagents to achieve thioesterification and scavenge unreacted thiol. In addn., catch-and-release purifn. has been employed to enable isolation of the aldehyde from silylthioether byproducts without the need for chromatog...