A practical procedure for the synthesis of multifunctional aldehydes through the Fukuyama reduction and elucidation of the reaction site and mechanism |
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Authors: | Mayumi Kimura |
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Affiliation: | Process Chemistry Research Laboratories, Tanabe Seiyaku Co., Ltd, 3-16-89, Kashima, Yodogawa-ku, Osaka 532-8505, Japan |
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Abstract: | A highly efficient heterogeneous Pd/C catalyst D1 was found to effect the reduction of thiol esters 1 to the corresponding aldehydes 2 with such a low catalyst loading as 0.5-1.0 mol %. The chemical properties of the Pd/C catalysts together with the XRF analysis reveal that the reduction is most likely to proceed on the solid surface of the Pd/C catalyst rather than in the solution phase outside the pores. A reaction mechanism through oxidative addition of Pd to the thiol esters 1 was postulated by detection of the oxidative addition intermediate by React IR analysis. A practical purification of 2 was accomplished by conversion to water-soluble bisulfite adducts 7. |
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