4.7 Article

Disilanes as oxygen scavengers and surrogates of hydrosilanes suitable for selective reduction of nitroarenes, phosphine oxides and other valuable substrates

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ORGANIC CHEMISTRY FRONTIERS
卷 4, 期 12, 页码 2437-2444

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c7qo00566k

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  1. Polish National Center of Sciences (NCN) [SONATA 10, 2015/19/D/ST5/02774]

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In this report, we demonstrate that the reaction of nitroarenes with hexamethyldisilane under various conditions affords a different range of compounds with excellent selectivity. In particular, the reaction of nitroarenes with hexamethyldisilane using a CsF/TBAB/toluene system provides suitable azo compounds, while in the presence of a CsF/TBAB/[Pd]/EtOH system hexamethyldisilane acts as a novel surrogate of gaseous trimethylsilane, thus, reducing nitroarenes to corresponding anilines. The synthetic value of the developed methodology was further extended by the reduction of a wide range of substrates including N-oxides, sulfoxides, phosphine oxides etc.

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