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Copper-mediated transformation of organosilanes to nitriles with DMF and ammonium iodide

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Title: Copper-mediated transformation of organosilanes to nitriles with DMF and ammonium iodide

Subject: ammonium iodide, ; copper, ; nitrile, ; quaternary ammonium derivative, ; silane derivative, ; article, ; catalysis, ; chemical structure, ; chemistry, ; combinatorial chemistry, ; oxidation reduction reaction, ; synthesis, ; Catalysis, ; Combinatorial Chemistry Techniques, ; Copper, ; Molecular Structure, ; Nitriles, ; Oxidation-Reduction, ; Quaternary Ammonium Compounds, ; Silanes

Abstract: Cyanation of aryl-, diaryldimethyl-, and styrylsilanes was developed for the first time under copper-mediated oxidative conditions using ammonium iodide and DMF as the combined source of nitrogen and carbon atom of the introduced cyano unit, respectively. The reaction was observed to proceed in a two-step process: initial conversion of organosilanes to their iodo intermediates and then cyanation. This method has a broad substrate scope with high functional group tolerance. © 2013 American Chemical Society.