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Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous‐Flow Hydrogenation‐Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts
Author(s) -
Miyamura Hiroyuki,
Tobita Fumiya,
Suzuki Aya,
Kobayashi Shū
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904159
Subject(s) - bimetallic strip , chemistry , catalysis , flow chemistry , derivatization , selectivity , continuous flow , nanoparticle , dehydrogenation , microreactor , decomposition , heterogeneous catalysis , combinatorial chemistry , organic chemistry , nanotechnology , materials science , high performance liquid chromatography , physics , mechanics
Pt–Au bimetallic nanoparticle catalysts immobilized on dimethyl polysilane (Pt–Au/(DMPSi‐Al 2 O 3 )) have been developed for selective hydrogenation of quinones to hydroquinones. High reactivity, selectivity, and robustness of the catalysts were confirmed under continuous‐flow conditions. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, methacrylation, and benzoylation were successfully performed under sequential and continuous‐flow conditions to afford the desired products in good to excellent yields. Especially, air‐sensitive hydroquinones, such as anthrahydroquinones and naphthohydroquinones, could be successfully generated and derivatized under closed sequential and continuous‐flow conditions without decomposition.