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Size of Gold Nanoparticles Driving Selective Amide Synthesis through Aerobic Condensation of Aldehydes and Amines
Author(s) -
Miyamura Hiroyuki,
Min Hyemin,
Soulé JeanFrançois,
Kobayashi Shū
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501795
Subject(s) - amide , imine , chemistry , selectivity , colloidal gold , nanoparticle , condensation , condensation reaction , primary (astronomy) , metal , combinatorial chemistry , amine gas treating , organic chemistry , catalysis , nanotechnology , materials science , physics , astronomy , thermodynamics
Abstract Metal nanoparticles (NPs) have attracted much attention in many fields due to their intrinsic characteristics. It is generally accepted that smaller NPs (1.5–3 nm) are more active than larger NPs, and reverse cases are very rare. We report here the direct aerobic oxidative amide synthesis from aldehydes and amines catalyzed by polymer‐incarcerated gold (Au) NPs. A unique correlation between imine/amide selectivity and size of NPs was discovered; Au‐NPs of medium size (4.5–11 nm) were found to be optimal. High yields were obtained with a broad range of substrates, including primary amines. Au‐NPs of medium size could be recovered and reused several times without loss of activity, and they showed good activity and selectivity in amide formation from alcohols and amines.