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                            The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
 
                
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    							Batch number can be found on the product's label following the word 'Batch'.
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Qiao Lin ; Ethan H. Spielvogel ; Tianning Diao ;
Abstract: The capture of carbon-centered radicals at a nickel(II) center is commonly featured in recent cross-coupling and metallaphotoredox catalytic reactions. Despite its widespread application in catalysis, this fundamental step lacks experimental characterization. This report portrays radical capture at catalytically relevant nickel(II) centers from several aspects, including the structure-activity relationships of the ligands, the mechanism, the kinetics, and the stereoselectivity. Spectroscopic data provide evidence for the formation of a nickel(III) intermediate. Strikingly different reactivity between nickel-aryl and nickel-alkyl complexes implies different rate-determining steps for C(sp3)–C(sp3) and C(sp2)–C(sp3) bond formation. Kinetic data benchmark the capture rates on the scale of 10[7] M−1s−1 and 10[6] M−1s−1 for primary and secondary radicals, respectively. Overall, the activation energy is higher than that of previous computational estimations. Finally, stoichiometric experiments with well-defined chiral nickel complexes demonstrate that the radical trapping step can confer diastereoselectivity and enantioselectivity with a drastic ligand effect.
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 complexes Spectroscopic evidence, rates, and selectivity.png) 
                        | CAS No. : | 605-39-0 | 
| Formula : | C14H14 | 
| M.W : | 182.26 | 
| SMILES Code : | CC1=CC=CC=C1C2=CC=CC=C2C | 
| MDL No. : | MFCD00048075 | 
| InChI Key : | ABMKWMASVFVTMD-UHFFFAOYSA-N | 
| Pubchem ID : | 11797 | 
| GHS Pictogram: |   | 
| Signal Word: | Warning | 
| Hazard Statements: | H315-H319-H335 | 
| Precautionary Statements: | P261-P305+P351+P338 | 
* 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 | 
|---|---|---|
| 90% | With magnesium; In water; at 100℃; for 2.5h;Sealed tube; | General procedure: 234mg of 4-methoxyiodobenzene (1 equiv., 1mmol) and100mg of Mg powder (4 equiv., 4mmol) were taken inscrew cap vial with catalyst coated cordierite monolith, suspendedin 4mL of water and refluxed. Completion of thereaction was checked with TLC and extracted with diethylether. Anhydrous sodium sulphate was added to organiclayer to remove trace amount of water and filtered. Solventwas evaporated in rotary evaporator. Product obtained waspurifed by column chromatography by taking 5% Ethylacetate in petroleum ether as eluent. All isolated productswere characterized by 1H NMR and 13C NMR. | 
| 83% | With potassium phosphate; In water; at 100℃; for 24h;Catalytic behavior; | General procedure: A mixture of Pd NPs-HNG nanocomposite (0.25-2 mol% of Pd),K3PO4(3 mmol), aryl halide (1.0 mmol), and 2 mL of H2O was stirredin air at 100C. After completion of the reaction as indicated by TLC,the heterogeneous mixture was cooled to room temperature andfiltered through a pad of celite. The filtrate was concentrated andthen the residue was purified by thin-layer chromatography (ethylacetate and n-hexane) to yield a pure product. The catalyst wasrecovered by filtration and washed extensively with acetone anddrying in the air. | 
| 80% | With potassium acetate; In ethanol; dimethyl sulfoxide; at 120℃; for 20h;Schlenk technique; Inert atmosphere; | General procedure: palladium catalyst (1.0 mol%) and KOAc (3 mmol) were placed in an oven dried 25 mL Schlenk tube, and the reaction vessel was evacuated and filled with nitrogen for three times. Aromatic halide (0.5 mmol), and solvent (5.0 mL) were added with a syringe, and the resulting mixture was stirred at 120 C for a desired time. After cooled down to room temperature, the reaction mixture was filtered and washed with brine and diethyl ether. The combined organic layers were washed with a saturated solution of sodium hydrogen carbonate and then with brine, dried over Na2SO4. Solvent was removed under a reduced pressure, and the reaction products were purifiedby silica gel chromatography with a mixture of n-hexane and ethyl acetate. | 
| 78% | With tetrabutylammonium nitrate; sodium hydroxide; palladium dichloride; at 120℃; for 7h;Catalytic behavior; | General procedure: Aryl halide (2.0 mmol) was added to a flask containingtetrabutylammonium nitrate (0.5 mmol, 0.15 g), PdCl2(0.03 mmol, 0.0053 g), and NaOH (2.0 mmol, 0.08 g),and the mixture was stirred at 120 C. After completion ofthe reaction, which was detected by TLC, the mixture wascooled to room temperature and the coupled product wasextracted with diethyl ether (3 × 3 mL). The solvent wasthen evaporated to leave the crude product, which was purifiedby column chromatography over silica gel using n-hexaneas the eluent to give the pure product. | 
| 65% | With triethylamine; In neat (no solvent); at 100℃; for 5h;Sealed tube; Irradiation; | General procedure: In a typical reaction, a mixture of aryl halid (0.25mmol),Et3N(0.25mmol) and TiO2-AA-Pd nanohybrid (0.3mol%)was added in a 10mL Pyrex test tube and sealed with septumcap. Then the reaction mixture transferred into a reactor chamber and irradiated under magnetic stirring using a CFL lamp (philips, wavelength in the range 390-750nm, 40W,1.1Wm-2) as the visible light source at 100C for appropriate time. After completion of the reaction, TiO2-AA-Pd nanohybrid was extracted by adding of ethanol (5ml) followedby centrifuging and decantation (3 × 5mL ethanol).Then, desired product (liquid phase) was extracted by platechromatography eluted with n-hexane/EtOAc (10/2). | 
| 28% | With triethylamine; In neat (no solvent); at 110℃; for 10h;Green chemistry; | General procedure: A mixture of aryl halide (0.125mmol), NEt3(0.375mmol)and catalyst (0.001g, 0.03mol%) was stirred at 110C forthe appropriate of time. The progress of the reaction was monitored by TLC. After completion of the reaction, Pd(II)NA2SMNP nanohybrid was extracted by adding of ethanol(5ml) followed by washing and decantation in the presenceof an external magnet (3 × 5ml ethanol). Then, desired product(liquid phase) was extracted by plate chromatographyeluted with n-hexane/EtOAc (10/1). | 
| 71.9%Chromat. | With porous chitosan microspheres supported palladium catalyst; In ethylene glycol; dimethyl sulfoxide; at 110℃; for 23h; | General procedure: To a 20 ml round bottom flask containing 5.0 ml of solvent, added aromatic halide (1.0 mmol), palladium catalyst (0.02 mmol) and potassium acetate (7.5 mmol). The resulting mixture was allowed to stir and the reaction progress was monitored by TLC and/or GC/MS analysis. The reaction was quenched with 10 ml water after completion and the mixture was extracted with ethyl acetate (3 × 20 ml). The combined organic extract was washed with water, saturated brine, and then dried with anhydrous Na2SO4. Solvent was removed under a reduced pressure, and the coupling product was purified by silica gel chromatography with petroleum ether and ethyl acetate. The homocoupling products are known and they are all consistent with the related chemical structures as characterized from 1H NMR and GC/MS analysis. | 

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 46%Chromat. | With potassium carbonate; In water; at 100℃; for 24h;Inert atmosphere; | General procedure: A mixture of aryl halide (0.5 mmol, 1.0 equiv.), phenylboronic acid (0.6 mmol, 1.2 equiv.), K2CO3 (2 mmol, 4equiv.), the Pd-NP-PIL catalyst (1.7 mol% based on the arylhalide substrate) in water (3 mL) was heated to 100 C under nitrogen with vigorous stirring for 4 h. The reaction mixture was then cooled at r.t. and the product was extracted with diethyl ether (3×3 mL). The combined extracts were washed with brine (15 mL), dried over anhydrous MgSO4, filtered and the solution was analyzed by GC. The structure of the products was also confirmed by 1H NMR spectroscopy. | 
Tags: 605-39-0 synthesis path| 605-39-0 SDS| 605-39-0 COA| 605-39-0 purity| 605-39-0 application| 605-39-0 NMR| 605-39-0 COA| 605-39-0 structure

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