Silver Cyanide Powder‐Catalyzed Selective Epoxidation of Cyclohexene and Styrene with its Surface Activation by H₂O_2(aq) and Assisted by CH₃CN as a Non‐Innocent Solvent

Abstract

We undertake silver cyanide (AgCN) powder for its catalytic epoxidation of cyclohexene or styrene in CH 3 CN with variable substrate-to-solvent volume ratios using H 2 O 2(aq) at 60 °C. The reaction mixtures can facilely separate into organic and aqueous layers. Cyclohexene oxide can be produced in the organic layer with 100 % selectivity from the substrate cyclohexene, while styrene oxide was identified with 80 % selectivity against benzaldehyde in styrene oxidation. After reactions, we can recycle the AgCN particles with comparable bulk property clarified via XRD, XPS, XAS, FT-IR, and 13 C-SS NMR spectroscopy. Using H 2 18 O 2 as the oxidant, both epoxide products and acetamide are highly enriched with 18 O-atom, indicating that the π bond-activation is essential for forming the cyclohexene/ styrene oxides in the organic and acetamide in the aqueous layers. The oxidation of cyclohexene/styrene catalyzed by AgCN powder through surface activation by H 2 O 2(aq) and assisted by the non-innocent CH 3 CN-originated acetamide can achieve highly selective π-bond activation with high reactivity.

Unprecedented iron-assisted room temperature synthesis of AgCN using acetonitrile

“…1a. 14,15 Markedly, no additional peaks indicative of Ag 2 O or Ag NPs were observed in the XRD pattern which circuitously supports the highly crystalline nature of the formed AgCN. 16,17 In the FT-IR analysis, the presence of a strong vibrational band at 2140 cm −1 and a weak band at 2163 cm −1 conrmed the existence of the -C^N bond.…”

“…This contributes to the revenue of mining companies and has a positive impact on both local and national economies. [14][15][16] Recognizing the substantial demand for silver extraction from Ag 2 S ore, we endeavored to reproduce the same reaction under standard conditions, following our successful synthesis of AgCN using AgNO 3 . Unfortunately, we did not observe the formation of AgCN in this instance.…”