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Co‐immobilization of Laccase and TEMPO in the Compartments of Mesoporous Silica for a Green and One‐Pot Cascade Synthesis of Coumarins by Knoevenagel Condensation
Author(s) -
MogharabiManzari Mehdi,
Amini Mohsen,
Abdollahi Mohammad,
Khoobi Mehdi,
Bagherzadeh Ghodsieh,
Faramarzi Mohammad Ali
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201701527
Subject(s) - knoevenagel condensation , chemistry , catalysis , one pot synthesis , mesoporous material , organic chemistry , laccase , mesoporous silica , green chemistry , malononitrile , reaction mechanism , enzyme
Co‐immobilization of bio‐ and chemocatalysts produces sustainable, recyclable hybrid systems that open new horizons for green cascade approaches in organic synthesis. Here, the co‐immobilization of laccase and 2,2,6,6‐tetramethylpiperidin‐1‐oxyl (TEMPO) in mesoporous silica was used for the one‐pot aqueous synthesis of 30 coumarin‐3‐carboxylate derivatives under mild conditions through the condensation of in situ oxidized 2‐hydroxybenzyl alcohols and malonate derivatives. A maximum yield was obtained after incubating at pH 6.0 and 45 °C for 24 h. An efficient organic synthesis was catalyzed by the hybrid catalyst in 10 % organic solvent. More than 95 % of the initial activity of the enzyme was preserved after 10 cycles, and no significant catalyst deactivation occurred after 10 runs. This new system efficiently catalyzed the in situ aerobic oxidation of salicyl alcohols, followed by Knoevenagel condensation, which confirmed the possibility of producing efficient hybrid catalysts by co‐immobilization of catalytic species in mesoporous materials.