Potassium Persulfate as an Eco-Friendly Oxidant for Oxidative Transformations

Abstract

The formation of carbon-carbon/carbon-heteroatom bonds by oxidative transformations is a hotly debated topic in chemistry. K2S2O8 has emerged as a cost-effective inorganic oxidant for a wide range of oxidative reactions in this setting. This book chapter covers oxidative reactions facilitated by K2S2O8 in the absence of a metal catalyst in detail. Organic chemists may find this book chapter valuable in formulating the mechanistic pathways involving the sulphate radical anion, as well as in the quick and environmentally friendly synthesis of novel chemical species.

Silver nitrate promoted synthesis of tetraphenyl derivatives and diaryl ketones

“…Column chromatography was performed using the MACHEREY-NAGEL silica gel 60 mit with a mixture of ethyl acetate/hexane or hexane as an eluent. 1 H NMR spectra were recorded on 400 MHz & 600 MHz, 13 C-NMR spectra were recorded on 100 MHz & 151 MHz, and Varian Mercury spectrometer using CDCl3 as solvent. The spectra were recorded and presented as chemical shifts (ppm).…”

“…The crude product was purified by column chromatography (Hexane, silica gel) and obtained as solid 2a-2d. Furthermore, the obtained desired products were characterized by NMR, the data are shown given below and the 1 H-NMR and 13 C-NMR spectra of the products were matched with the literature data. 25,26 © AUTHOR(S) General procedure for synthesis of aryl ketones derivatives.…”

“…7 After the reaction according to the general procedure: 9H-fluorene (0.2 mmol), silver nitrate (0.04 mmol), potassium persulfate (0.2 mmol) in the acetonitrile and water (1:1) ratio were added. The resulting mixture was stirred under nitrogen atmosphere at 60 °C for 24 h. The crude mixture was purified by column chromatography (silica gel) using hexane as solvent and obtained as white solid (26.5 mg, 40%); mp 241-242 °C ; 1 H-NMR (400 MHz, CDCl3) δ 7.65 (d, J = 8.0 Hz, 4H), 7.29 (d, J = 8.0 Hz, 4H),7.10 (t, J = 8.0 Hz, 4H), 6.96 (d, J = 8.0 Hz, 4H), 4.85(s,2H); 13 C-NMR (100 MHz, CDCl3) δ 144.6, 141.5, 127.3, 126.7, 124.0, 119.6, 49.8 9H,9'H-9,9'-Bixanthene (2d). 31 After the reaction according to the general procedure: 9H-xanthene (0.2 mmol), silver nitrate (0.04 mmol), potassium persulfate (0.2 mmol) in the ratio of acetonitrile and water (1:1).…”

“…The resulting mixture was stirred under nitrogen atmosphere at © AUTHOR(S) 60 °C for 24 h. The crude mixture was purified by column chromatography (silica gel) using hexane as solvent and obtained as white solid (22 mg, 50%); mp 101-102 °C ; 1 H-NMR (400 MHz, CDCl3) δ 7.84-7.80 (m, 4H), 7.19-7.15 (m, 4H); 13 34 After the reaction according to the general procedure: 1benzyl-2-(trifluoromethyl)benzene (0.2 mmol), silver nitrate (0.4 mmol), potassium persulfate (0.2 mmol) in acetonitrile and water (1:1) ratio were added. The resulting mixture was stirred under nitrogen atmosphere at 60 °C for 24 h. The crude mixture was purified by column chromatography (silica gel) using hexane as solvent and obtained as white solid (24 mg, 48%); mp 60-61 °C ; 1 H-NMR (400 MHz, CDCl3) δ 7.79-7.77 (m, 3H), 7.64-7.58 (m, 3H), 7.47-7.43 (m, 2H), 7.40-7.37 (m, 1H); 13 C-NMR (100 MHz, CDCl3) δ 198.9, 138.4, 136.5, 134.0, 131.5, 130.3, 129.9, 128.6, 128.2, 126.8 (q, JC-F =4.6 Hz), 123.7 (d, JC-F 272.2Hz) (4-(Dimethylamino)phenyl)(phenyl)methanone (3d). 32 After the reaction according to the general procedure: 4-benzyl-N,N-dimethylaniline (0.2 mmol), silver nitrate (0.4 mmol), potassium persulfate (0.2 mmol) in acetonitrile and water (1:1) ratio were added.…”

“…Silver catalysts combined with K2S2O8 allow for various oxidative C-H bond functionalizations to generate distinct C-C, C-O, and C-N bonds. [12][13][14] Herein, a novel silver-mediated oxidative homocoupling strategy is presented, facilitating the coupling of two molecules of the same substrate. In contrast, diarylketones are well known compounds that are widely employed in the synthesis of various applications.…”