Open AccessSilver-Nanoparticle-Catalyzed Dearomatization of Indoles toward 3-Spiroindolenines via a 5-exo-dig Spirocyclization
Author(s) -
Felix Schrӧder,
Upendra K. Sharma,
Martijn Mertens,
François Devred,
Damien P. Debecker,
Rafael Luque,
Erik V. Van der Eycken
Publication year - 2016
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.6b02443
Subject(s) - catalysis , x ray photoelectron spectroscopy , diastereomer , chemistry , adduct , nanoparticle , inductively coupled plasma atomic emission spectroscopy , transmission electron microscopy , metal , inductively coupled plasma , spectroscopy , leaching (pedology) , nuclear chemistry , organic chemistry , chemical engineering , materials science , nanotechnology , plasma , physics , environmental science , quantum mechanics , soil science , engineering , soil water
We present a supported silver-nanoparticle-catalyzed dearomatization of 3-substituted indoles toward 3-spiroindolenines. Two scaffolds were investigated for this transformation. The yields range from moderate to high. In the case of chiral reactants (Ugi four-component reaction adducts), the process is diastereoselective with a diastereomeric excess between 75% and 92%. The catalyst was characterized by transmission electron microscopy (TEM) and X-ray photoelectron spectroscopy (XPS). Metal leaching was investigated using hot-filtration and inductively coupled plasma-atomic emission spectroscopy (ICP-AES) experiments. An apparent turnover frequency (TOF) was determined.status: publishe
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