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CAS No. : | 13922-41-3 | MDL No. : | MFCD00019722 |
Formula : | C10H9BO2 | Boiling Point : | - |
Linear Structure Formula : | (HO)2BC10H7 | InChI Key : | HUMMCEUVDBVXTQ-UHFFFAOYSA-N |
M.W : | 171.99 | Pubchem ID : | 254532 |
Synonyms : |
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Chemical Name : | Naphthalen-1-ylboronic acid |
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: |
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* 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 |
---|---|---|
95% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; at 70.0℃;Inert atmosphere; Sealed tube; | General procedure: A bromo-aldehyde (1 mmol), boronic acid (1.1e1.3 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate(3 mmol), water (3 ml), ethanol (4 ml) and toluene (4 ml)were added to a round-bottomed flask. The reaction mixture wasflushed with argon, sealed under septa and heated at 70 C overnight.After cooling to room temperature, water (50 ml) was added,and product was extracted with ethyl acetate (3 x 50 ml). Combinedextracts were washed with brine, dried with anhydrousmagnesium sulfate and evaporated under reduced pressure. Theproduct was purified by column chromatography on silica withchloroform or a mixture of methanol and chloroform (1:9). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Inert atmosphere; | 1-(8-naphthyl)-isoquinoline (8-NAIQ). 1-(8-naphthyl)-isoquinoline was obtained from thereaction of <strong>[63927-22-0]8-bromoisoquinoline</strong> and naphthalene-1-boronic acid by Suzuki coupling [8]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; for 0.166667h;Microwave irradiation; | First, into a recovery flask equipped with a reflux pipe were put 2.05 g of <strong>[38557-72-1]2-chloro-3,5-dimethylpyrazine</strong>, 2.48 g of 1-naphthylboronic acid, 1.53 g of sodium carbonate, 0.066 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes, whereby heating was performed. After that, water was added to this solution, and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. Accordingly, Hdm1npr (a light orange powder, 59% yield), which was the substance to be produced, was obtained. Note that the irradiation with microwaves was performed using a microwaves synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 1 is shown in (a-1) below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 1-(7-benzofuranyl)-2-di(3,5-di-tert-butyl-4-methoxyphenyl)phosphinenaphthalene; In toluene; at 80℃; for 10h;Glovebox; Inert atmosphere; | In a glove box, 1.0 mmol of a halogenated aromatic or heterocyclic aromatic hydrocarbon compound, 2.0 mmol of 1-naphthylboronic acid, Pd2 (dba) 3, a phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen,After heating to 80 ° C, the reaction was carried out for a period of time. The results are shown in Table 1. The amount of Pd2 (dba) 3 and the phosphine ligand is divided into three types: (1) 0.25 molpercent Pd2 (dba) 3, 0.5 molpercent phosphine ligand, or (2) 0.5 molpercent Pd2 (dba) molpercent phosphine ligand, or (3) 1.0 molpercent Pd2 (dba) 3, 2.0 molpercent phosphine ligand, depending on the amount of ligand used in Table 1. |
81% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); C38H31O5P; In toluene; at 80℃; for 8h;Inert atmosphere; Glovebox; | General procedure: In the glove box, Sm5 (0.1 mmol, 1.0 equiv), Sm2 (0.2 mmol, 2.0 equiv), K3PO4 (0.3 mmol, 3.0 equiv), Pd2(dba)3 (1.0percent mmol), (±)-8A (2.0percent mmol) and toluene (4.0mL) were added into a 25 mL single-necked flask, the reaction was stirred at 80 deg. C under nitrogen for 8 hours. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.3% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 24h;Inert atmosphere; | <strong>[1000623-95-9]3,6-bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione</strong> (150.2mg, 0.22mmol) and 1-naphthyl boronic acid (113.4mg, 0.66mmol) was dissolved in 15mL toluene solution, then add 3mL of ethanol and 2mL aqueous sodium carbonate (sodium carbonate 186.5mg, 1.76mmol), After nitrogen gas was purged for 20 min, tetrakistriphenylphosphine palladium (10.2 mg, 0.0088 mmol) was added, and the mixture was heated to 100 C for 24 hours under nitrogen atmosphere, and then cooled to room temperature. Water and extracted three times with dichloromethane, the extract was dried over anhydrous magnesium sulfate, filtered to obtain the organic solution, the solvent was removed under reduced pressure, chromatographed on silica gel column with petroleum ether/ethyl acetate = 10:1 (v/v) as eluent, to give the crude product, then recrystallized from isopropanol, to obtain the pure black product 129.1mg, yield 75.3% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene;Inert atmosphere; Reflux; | A Straus flask equipped with a stirrer bar was charged with 2-bromopyridine (1.0 equiv.), 1-naphthylboronic acid (1.1 equiv),Pd(PPh3)4 (4 mol%), 2 M aq Na2CO3 (2.5 mL/mmol), toluene(3.8 mL/mmol), and ethanol (1.3 mL/mmol). The mixture wasdegassed by three freeze-pump-thaw cycles and then refluxedunder inert conditions overnight. The mixture was cooled to r.t.and extracted with EtOAc (3 × 20 mL). The organic phases werecombined, dried (MgSO4), and concentrated. The pure ligandwas obtained by flash column chromatography [silica gel,EtOAc-hexane (1:4)].Compound was isolated as viscous liquid that solidified uponstanding. Yield: 1.6 g (99%). |