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Issue 21, 2018
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A new anthraquinoid ligand for the iron-catalyzed hydrosilylation of carbonyl compounds at room temperature: new insights and kinetics

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Abstract

The reaction of 1-((2-(pyridin-2-yl)ethyl)amino)anthraquinone with either Fe(HMDS)2 or Li(HMDS)/FeCl2 allowed the preparation of a new anthraquinoid-based iron(II) complex active in the hydrosilylations of carbonyls. The new complex Fe(2)2 was characterized by single-crystal X-ray diffraction, infrared spectroscopy, NMR, and high resolution mass spectrometry (electrospray ionization). Superconducting quantum interference device (SQUID) magnetometry established no spin crossover behavior with an S = 2 state at room temperature. This complex was determined to be an effective catalyst for the hydrosilylation of aldehydes and ketones, exhibiting turnover frequencies of up to 63 min−1 with a broad functional group tolerance by just using 0.25 mol% of the catalyst at room temperature, and even under solvent-free conditions. The aldehyde hydrosilylation makes it one of the most efficient first-row transition metal catalysts for this transformation. Kinetic studies have proven first-order dependences with respect to acetophenone and Ph2SiH2 and a fractional order in the case of the catalyst.

Graphical abstract: A new anthraquinoid ligand for the iron-catalyzed hydrosilylation of carbonyl compounds at room temperature: new insights and kinetics

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Publication details

The article was received on 23 Mar 2018, accepted on 23 Apr 2018 and first published on 24 Apr 2018


Article type: Paper
DOI: 10.1039/C8DT01123K
Citation: Dalton Trans., 2018,47, 7272-7281
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    A new anthraquinoid ligand for the iron-catalyzed hydrosilylation of carbonyl compounds at room temperature: new insights and kinetics

    Á. Raya-Barón, C. P. Galdeano-Ruano, P. Oña-Burgos, A. Rodríguez-Diéguez, R. Langer, R. López-Ruiz, R. Romero-González, I. Kuzu and I. Fernández, Dalton Trans., 2018, 47, 7272
    DOI: 10.1039/C8DT01123K

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