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Highly Efficient Aqueous Synthesis of Propargylamines through C–H Activation Catalyzed by Magnetic Organosilica‐Supported Gold Nanoparticles as an Artificial Metalloenzyme
Author(s) -
Aghahosseini Hamideh,
Tabatabaei Rezaei Seyed Jamal,
Tadayyon Mahsa,
Ramazani Ali,
Amani Vahid,
Ahmadi Roya,
Abdolahnjadian Davod
Publication year - 2018
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201800085
Subject(s) - chemistry , nanoparticle , catalysis , ionic liquid , alkyl , aqueous solution , ligand (biochemistry) , pyridinium , colloidal gold , magnetic nanoparticles , halide , combinatorial chemistry , inorganic chemistry , organic chemistry , chemical engineering , biochemistry , receptor , engineering
Highly efficient magnetic organosilica‐supported gold nanoparticles were developed as an artificial metalloenzyme for the synthesis of propargylamines through C–H activation in water under an ambient atmosphere. Herein, we present a very simple and efficient method for the deposition of Au nanoparticles on porous magnetic organosilica (Fe 3 O 4 @SiO 2 ‐Cl) through the thermal reduction of an organometallic Au III complex. As a nucleophile, a Au III polypyridyl coordination complex could react with alkyl halides from the Fe 3 O 4 @SiO 2 ‐Cl to form a quaternary ammonium salt as an ionic liquid; subsequently, the ligand was oxidized and the Au nanoparticles were embedded into the porous organosilica shell. The synergic effect of the gold nanoparticles as catalytically active sites, pyridinium chloride as a phase‐transfer agent, and the magnetite nanoparticle core, which could function as a protein mimic, endow the material with high efficiency, stability, recoverability, reusability, and good turnover frequency, all of which are necessary characteristic for an artificial enzyme. A reliable catalytic procedure for the synthesis of propargylamines was identified.