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Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon , et al. ACS Appl. Nano Mater.,2022,5(12):18603-18611. DOI: 10.1021/acsanm.2c04393
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Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.
Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki?Miyaura coupling reaction ; size-selective reaction ; catalyst processing
Purchased from AmBeed: 128796-39-4 ; 10365-98-7 ; 98-80-6 ; 556-96-7 ; 171663-13-1 ; 71597-85-8 ; 402-43-7 ; 2042-37-7 ; 22385-77-9 ; 16419-60-6 ; 15862-18-7 ; 87199-15-3 ; 171408-84-7 ; 643-58-3 ; 591-50-4 ; 76911-73-4 ; 398-36-7 ; 14871-92-2 ; 5720-07-0 ; 945976-76-1 ; 366-18-7 ; 2920-38-9 ; 623-00-7 ; 24973-49-7 ; 588-59-0 ; 128796-39-4 ; 5723-93-3 ; 17057-88-4 ; 126485-55-0 ...More
CAS No. : | 556-96-7 | MDL No. : | MFCD00000087 |
Formula : | C8H9Br | Boiling Point : | - |
Linear Structure Formula : | C6H3(CH3)2Br | InChI Key : | LMFRTSBQRLSJHC-UHFFFAOYSA-N |
M.W : | 185.06 | Pubchem ID : | 136357 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | Placing Compound A in an amount of 25.2 g (136 mmol) and KMnO4 in an amount of 86.1 g (544 mmol) into a flask, and the resultant solution was reacted in water for 9 hours under refluxing. After the reaction terminated, a precipitate was filtered and the filtrate was processed with 6N hydrochloric acid at room temperature. A deposit was washed with the use of 0. 1N hydrochloric acid and dried, resultantly obtaining 11.4 g of Intermediate B (yield: 34 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With potassium cyanide; CuI; In dodecane; ethyl acetate; toluene; | Example 216 3,5-Dimethylbenzonitrile from 5-bromo-m-xylene and Potassium Cyanide using N,N'-dimethylethylenediamine as Ligand A Schlenk tube was charged with CuI (19.5 mg, 0.102 mmol, 20 mol %), KCN (78 mg, 1.20 mmol), evacuated, backfilled with Ar. N,N'-Dimethylethylenediamine (21.5 muL, 0.202 mmol, 20 mol %), 5-bromo-m-xylene (136 muL, 1.00 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110 C. for 24 h. Dodecane (internal GC standard, 230 muL), ethyl acetate (2 mL), and 30% aq ammonia (1 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide a 15% yield of 3,5-dimethylbenzonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With potassium permanganate; water; at 80℃; for 2.25h; | l-bromo-3,5-dimethylbenzene (15 g, 81 mmol, 1.0 eq) in a mixture of pyridine (133 mL) and H20 (83 mL) was heated to 80C. KMn04 (25.6 g, 162 mmol, 2.0 eq) was added in portions over 45 min. After the addition was completed, heating was continued at 80C for 1.5 h. The hot solution was then filtered, and the filtrate was acidified by addition of concentrated hydrochloric acid. The aqueous solution was extracted with EtOAc and the combined organic extracts washed with water and brine, dried (Na2SC>4), filtered and evaporated in vacuo. The residue was purified by column chromatography (CH2C12: MeOH, 80: 1 to 40: 1) to give the title compound as a white solid (5.2 g, 29 %)LC-MS: m z 212.9, 215 [M+H]+ 1H NMR (400 MHz, MeOD) delta 7.91 (s, 1H), 7.79 (s, 1H), 7.57 (s, 1H), 2.38 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
146.1 mg | With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 35℃; for 72h;Inert atmosphere; Glovebox; | General procedure: Unless otherwise stated, in an Argon filled glove-box a crimp-cap microwave vial equipped with a magnetic stirring bar was charged with the appropriate cyclometalated Ru(ll)-catalyst (like Ru1-Ru46, from 3 mol % to 10 mol %), KOAc (5.9 mg, 0.06 mmol, 30 mol %), K2CO3 (2.0 - 4.0 equiv.), the appropriate DG-containing arene (like N1-N12, 0.20 mmol, 1.0 equiv.), the appropriate (hetero)aryl (pseudo)halide (like X1-X42, 0.2 mmol, 1.0 equiv) and /V-methyl-2- pyrrolidone (NMP) (200 pL, 1 M). The vial was capped and stirred at 35 C for 24 hours. Upon completion, the crude mixture was loaded on a silica gel column and purified by flash chromatography |