Fukuyama Reduction and Integrated Thioesterification/Fukuyama Reduction of Thioesters and Acyl Chlorides Using Continuous Flow.
M Asadi, S Bonke, A Polyzos, DW Lupton
ACS Catal. | American Chemical Society | Published : 2014
Fukuyama redn. of thioesters has been achieved using a polymer-supported Pd 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...View full abstract
D.W.L. thanks the ARC for financial support through the Future Fellowship and Discovery programs. D.W.L. and A.P. thank the CSIRO Flagship Collaboration Research Fund for seed funding. The authors acknowledge the use of facilities within the Monash Centre for Electron Microscopy.