Silver-Nanoparticle-Catalyzed Dearomatization of indoles toward 3-Spiroindolenines via a 5-exo-dig Spirocyclization

Schröder, Felix;Sharma, Upendra K.;Mertens, Martijn;Devred, François;Debecker, Damien;et.al.
(2016) ACS Catalysis — Vol. 6, p. 8156-8161 (2016)

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Abstract
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.
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  • Institution iconUCLouvainSST/IMCN/MOST - Molecules, Solids and Reactivity

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Schröder, F., Sharma, U. K., Mertens, M., Devred, F., Debecker, D., & et al. (2016). Silver-Nanoparticle-Catalyzed Dearomatization of indoles toward 3-Spiroindolenines via a 5-exo-dig Spirocyclization. ACS Catalysis, 6, 8156-8161. https://doi.org/10.1021/acscatal.6b02443 (Original work published 2016)