Sulfonic acid anchored on silica, SiO2@SO3H: A superior solid acid catalyst for quick and solvent-free reductive-deoxygenation of ketones with NaBH3CN

Zeynizadeh, B and Kouhkan, M (2018) Sulfonic acid anchored on silica, SiO2@SO3H: A superior solid acid catalyst for quick and solvent-free reductive-deoxygenation of ketones with NaBH3CN. J Chin Chem Soc, 65. pp. 1521-1528.

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Abstract

NaBH3CN as a modified hydroborate agent and due to a strong withdrawing CN group does not show any reducing ability to reduce functional groups in the absence of acidic media (pH ~ 3–4). In this study, the immobilized sulfonic acid on silica, SiO2@SO3H, was prepared and applied as a new solid acid catalyst for extremely enhancing the reducing ability of NaBH3CN. The influence of SiO2@- SO3H was highlighted by performing the quick and green reduction of structurally diverse carbonyl compounds involving aldehydes, ketones, α,β-unsaturated enals and enones, α-diketones, and acyloins to the corresponding alcohols or alkanes with NaBH3CN. By the NaBH3CN/SiO2@SO3H system, aldehydes were reduced to the corresponding alcohols and ketonic compounds to alkanes as reductivedeoxygenation products. All reduction reactions were carried out within 3 min at room temperature and under solvent-free conditions to afford the products in high to excellent yields (90–98%).

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