Silver-Nanoparticle-Catalyzed Dearomatization of Indoles toward 3-Spiroindolenines via a 5-exo-dig Spirocyclization
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- 作者：Felix Schröder ; Upendra K. Sharma ; Martijn Mertens ; François Devred ; Damien P. Debecker ; Rafael Luque ; Erik V. Van der Eycken
- 刊名：ACS Catalysis
- 出版年：2016
- 出版时间：December 2, 2016
- 年：2016
- 卷：6
- 期：12
- 页码：8156-8161
- 全文大小：567K
- ISSN：2155-5435
文摘
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.