| 94% |
With oxygen; sodium t-butanolate In dimethyl sulfoxide at 50℃; for 5h; Sealed tube; |
2) General procedure for autoxidative oxygenation
General procedure: To a predried 5 mL round-bottom flask diarylmethane 1 (0.4 mmol), dry DMSO (1 mL), andt-BuONa (0.8 mmol) were subsequently added as soon as possible. The reaction system wassealed by a rubber septum with a needle connected to an O2 balloon, and then stirred at 50 oC for5 h. During this period, the reaction system suffered complex color changes. Then the reactionmixture was allowed to cool at room temperature, and diluted with 1 mol/L HCl to pH = 6-7,washed with ethyl acetate (20 mL × 3), dried over anhydrous Na2SO4, and filtered to get clearorganic solution. The solvent was removed reduced pressure by a rotary evaporator, and theresulting residue was subjected to column chromatography on silica gel using co-solvent (ethylacetate / petroleum ether = 1/20, v/v) as eluent to give the corresponding diarylketones. |
| 92% |
With tert.-butylhydroperoxide; C40H48AuN4(1+)*BF4(1-) In pyridine at 90℃; for 18h; |
|
| 87% |
With lithium perchlorate In water; acetonitrile at 20℃; for 5h; Electrolysis; |
|
| 71% |
With oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 12h; Schlenk technique; Irradiation; Green chemistry; |
|
| 66% |
With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; for 32h; |
AIBN/O2 initiated oxidation of diphenylmethane
General procedure: A solution of 1a (0.5 mmol) and AIBN (1.5 mmol) in MeCN (10 mL) was stirred at 75 oC under O2 atmosphere. After completion monitored by TLC (by UV visualization), the solvent was removed under reduced pressure. The products were separated by silica gel column chromatography eluted with petroleum ether/ ethyl acetate (v/v 30:1) to afford the product in pure form. |
| 65% |
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,1,2,2-tetrachloroethane at 130℃; for 24h; Autoclave; |
2 3.2 A typical procedure for DDQ/TBN-catalyzed aerobic oxidation of diarylmethanes
General procedure: A Teflon-lines 316 L stainless steel autoclave (300 mL) equipped with magnetic stirring bar was charged with substituted diarylmethanes 1 (2 mmol), 136.2 mg DDQ (0.6 mmol, 30 mol %), 41.2 mg TBN (0.4 mmol, 20 mol %), 480 mg acetic acid (8 mmol) and 20 mL TeCA. The autoclave was closed and charged with oxygen to 0.3 MPa. Then the autoclave was placed in an oil bath, which was preheated to 130 °C. The mixture was then stirred for a certain time until the reaction was completed. The autoclave was taken out from the oil bath, cooled to room temperature and carefully depressurized. The mixture was concentrated under reduced pressure and purified by column chromatography to give the desired diarylketones. |
| 62% |
With cercosporin; oxygen; potassium bromide In methanol at 20℃; Irradiation; Schlenk technique; Green chemistry; chemoselective reaction; |
|
| 54% |
With water; Selectfluor; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 12h; Sealed tube; Inert atmosphere; Irradiation; |
|
|
With dihydrogen peroxide; trifluoroacetic acid; zinc dibromide In 1,4-dioxane; water at 100℃; for 16h; |
General procedure for the oxidation of diphenylmethane to benzophenone
General procedure: In a 25 mL pressure tube, ZnBr2 (10 mol %) and a stirring bar were added. After the addition of diphenylmethane (1 mmol), trifluoroacetic acid (0.2 mL) and 1,4-dioxane (2 mL) by syringe, H2O2 (4 mmol; 30% aqueous) was added in one pot to the solution and the final solution was kept at 100 °C for 16 h. Then hexadecane (100 mg) and ethyl acetate (3 mL) were injected, a part of solution was taken for GC and GC-MS analysis after properly mixed. All the products are commercially available. |
|
With ketoreductase-P1-B12; oxygen; NADPH; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 23℃; for 24h; Irradiation; Enzymatic reaction; |
|
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