Visible-Light-Induced Cleavage of C−S Bonds in Thioacetals and Thioketals with Iodine as a Photocatalyst

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Abstract

A protocol for a visible-light-induced cleavage of thioacetals and thioketals using molecular iodine as a photocatalyst in combination with oxygen as the terminal oxidant is reported. The reaction proceeds with low catalyst loadings and high chemical yields while the most commonly used N- and O-protecting groups remain untouched in this transformation. Further investigation showed that the reaction also permits the synthesis of unsymmetrical disulfides by cleavage of unsymmetrical thioacetals.

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Krumb, M., Kammer, L. M., Forster, R., Grundke, C., & Opatz, T. (2020). Visible-Light-Induced Cleavage of C−S Bonds in Thioacetals and Thioketals with Iodine as a Photocatalyst. ChemPhotoChem, 4(2), 101–104. https://doi.org/10.1002/cptc.201900231

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