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Sulfonic acid anchored on silica, SiO 2 @SO 3 H: A superior solid acid catalyst for quick and solvent‐free reductive‐deoxygenation of ketones with NaBH 3 CN
Author(s) -
Zeynizadeh Behzad,
Kouhkan Mehri
Publication year - 2018
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201800250
Subject(s) - chemistry , deoxygenation , catalysis , sulfonic acid , solvent , reducing agent , organic chemistry
NaBH 3 CN 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, SiO 2 @SO 3 H, was prepared and applied as a new solid acid catalyst for extremely enhancing the reducing ability of NaBH 3 CN. The influence of SiO 2 @SO 3 H 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 NaBH 3 CN. By the NaBH 3 CN/SiO 2 @SO 3 H system, aldehydes were reduced to the corresponding alcohols and ketonic compounds to alkanes as reductive‐deoxygenation 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%).