2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
phenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With potassium hydrogen difluoride In methanol at 20℃; for 0.25h; Stage #2: With lithium hydroxide In acetonitrile at 20℃; for 20h; | 100% |
With hydrogenchloride In water at 20℃; for 15h; | 100% |
With polystyrene boronic acid; trifluoroacetic acid In acetonitrile for 18h; Heating; | 98% |
Multi-step reaction with 2 steps 1: diethyl ether / 0.5 h / 20 °C 2: hydrogenchloride / water / 0.33 h View Scheme | |
With dimyristoylphosphatidylcholine; water In dimethyl sulfoxide at 20℃; for 168h; |
1-chloro-3,5-dimethylbenzene
A
3,5-dimethylbiphenyl
B
phenylboronic acid
Conditions | Yield |
---|---|
With cesium fluoride; Pd(dba)2 In toluene | A n/a B 99% |
Conditions | Yield |
---|---|
In methanol at 15℃; for 3h; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With montmorillonite K10 at 25℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature; | 97% |
With 1H-imidazole; iron(III) chloride at 20℃; for 0.25h; Catalytic behavior; Solvent; Reagent/catalyst; Time; Inert atmosphere; | 87% |
With glass or Cs2CO3 In tetrahydrofuran; water Kinetics; hydrolysis at 55°C in THF/H2O in the presence of glass powder or Cs2CO3; not isolated; |
dihydroxy-methyl-borane
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
phenylboronic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; Reagent/catalyst; Solvent; | 97% |
Conditions | Yield |
---|---|
With borane; water In tetrahydrofuran for 1h; Heating; | 96% |
Conditions | Yield |
---|---|
at -78 - -45℃; | 95% |
diisopropopylaminoborane
water
phenylmagnesium bromide
phenylboronic acid
Conditions | Yield |
---|---|
Stage #1: diisopropopylaminoborane; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran at 0℃; for 0.583333h; Inert atmosphere; | 95% |
diisopropylamine borane
water
phenylmagnesium bromide
phenylboronic acid
Conditions | Yield |
---|---|
Stage #1: diisopropylamine borane; phenylmagnesium bromide In tetrahydrofuran at 20℃; Stage #2: water In tetrahydrofuran; methanol | 95% |
Conditions | Yield |
---|---|
excess acid addn. to soln. of Sb-compd., refluxing (3 h), volatile products collecting in cooled trap; products sepn. by ether; | A 94% B 92% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Temperature; Concentration; Flow reactor; | 93.9% |
Conditions | Yield |
---|---|
In methanol at 15℃; for 3h; Microwave irradiation; | 92% |
With [{Pd(μ-Cl){κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; sodium acetate In dichloromethane; water at 40℃; for 6h; Inert atmosphere; | |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 80℃; for 4h; Miyaura Borylation Reaction; Schlenk technique; Inert atmosphere; Sealed tube; |
dicyclohexylamine borane complex
water
phenylmagnesium bromide
phenylboronic acid
Conditions | Yield |
---|---|
Stage #1: dicyclohexylamine borane complex; phenylmagnesium bromide In tetrahydrofuran at 20℃; Stage #2: With methanol In tetrahydrofuran Stage #3: water In tetrahydrofuran | 92% |
Conditions | Yield |
---|---|
With bis(pinacol)diborane; Ir(o-O-C6H4-CH=N=CH2Ph)(cod) at 80℃; for 21h; Product distribution; Further Variations:; Solvents; | 91% |
Stage #1: benzene With Pinacolborane; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer at 80℃; for 24h; Stage #2: With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 17h; | |
Multi-step reaction with 2 steps 1: Pd 2: H2O View Scheme |
Conditions | Yield |
---|---|
With tetra-2-pyridinylpyrazine; [Ir(I)(salicylidenebenzyliminato)(1,5-cyclooctadiene)] In dichloromethane; benzene under Ar; mixt. was heated at 80°C for 21 h in mixt. of 3 ml benzene and 2 ml each CH2Cl2 and ionic liquid TBPD (tributyltetradecylphosphonium dodecylbenzenesulfonate) as solvent; solvent was removed under reduced pressure, Et2O was added, after 10% aq. HCl was added, mixt. stirred for 4 h, organic layer dried with MgSO4, solvent was removed under reduced pressure, residue was chromd. (flash chromy, SiO2); NMR; | 91% |
With tetra-2-pyridinylpyrazine; [Ir(I)(salicylidenebenzyliminato)(1,5-cyclooctadiene)] In benzene under Ar; soln. of Ir complex and pyridinylpyrazine was prepared, pinacolato soln. was added, mixt. was then heated at 80°C for 21 h; solvent was removed under reduced pressure, Et2O was added, after 10% aq. HCl was added, mixt. stirred for 4 h, organic layer dried with MgSO4, solvent was removed under reduced pressure, residue was chromd. (flash chromy, SiO2); NMR; | 70% |
With tetra-2-pyridinylpyrazine; [Ir(I)(salicylidenebenzyliminato)(1,5-cyclooctadiene)] In benzene High Pressure; under Ar; soln. of Ir complex and pyridinylpyrazine was prepared in glove box, pinacolato soln. and prepared catalyst and ligand soln. were placed in autoclave, mixt. was then heated at 100°C for 40 h; solvent was removed under reduced pressure, Et2O was added, after 10% aq. HCl was added, mixt. stirred for 4 h, organic layer dried with MgSO4, solvent was removed under reduced pressure, residue was chromd. (flash chromy, SiO2); NMR; | 67% |
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane; benzene other Radiation; under Ar atm. mixt. HBpin, nano-Ir(0) cat. prepd by reduction (Ph3P)2Ir(H)(7,8-nido-C2B9H11), tetra-2-pyridinylpyrazine, benzene, CH2Cl2 and trihexyltetradecylphosphonium methylsulfonate was heated at 130°C for 1 h in microwave, hydrolysis aq.HCl; flash chromy.; | 91% |
With hydrogenchloride In dichloromethane; benzene Sonication; under Ar atm. mixt. HBpin, nano-Ir(0) cat. prepd by reduction (Ph3P)2Ir(H)(7,8-nido-C2B9H11), tetra-2-pyridinylpyrazine, benzene, CH2Cl2 and trihexyltetradecylphosphonium methylsulfonate was heated at 80°C for4 h in ultrasonic, hydrolysis aq.HCl; flash chromy.; | 61% |
With hydrogenchloride In dichloromethane; benzene High Pressure; under Ar atm. mixt. HBpin, nano-Ir(0) cat. prepd by reduction (Ph3P)2Ir(H)(7,8-nido-C2B9H11), tetra-2-pyridinylpyrazine, benzene, CH2Cl2 and trihexyltetradecylphosphonium methylsulfonate was heated at 180°C for 12 h, hydrolysis with aq.HCl; flash chromy.; | 50% |
Conditions | Yield |
---|---|
With acetic acid In water | 90% |
methanol
bromobenzene
diisopropylamine borane
phenylboronic acid
Conditions | Yield |
---|---|
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: bromobenzene In tetrahydrofuran at 70℃; Stage #3: methanol Further stages; | 88% |
phenylboronic acid
Conditions | Yield |
---|---|
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 0.5h; | 86% |
With water; silica gel at 20℃; for 4h; Inert atmosphere; | 65% |
In phosphate buffer pH=6.9 - 7.0; Kinetics; | |
With water In tetrahydrofuran at 55℃; Kinetics; Reagent/catalyst; |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; | 82.7% |
With n-butyllithium In tetrahydrofuran |
Conditions | Yield |
---|---|
Stage #1: bromobenzene With triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 65℃; Stage #2: With sodium hydroxide In tetrahydrofuran Further stages.; | 82% |
Stage #1: bromobenzene With Trimethyl borate In tetrahydrofuran at -20 - 0℃; Inert atmosphere; Stage #2: With sulfuric acid In tetrahydrofuran at 0 - 10℃; for 10h; Inert atmosphere; | 82.4% |
Stage #1: bromobenzene With magnesium In tetrahydrofuran Stage #2: With Trimethyl borate In tetrahydrofuran at -70℃; | 82.4% |
Conditions | Yield |
---|---|
With 1H-imidazole; thionyl chloride In acetonitrile the B complex was obtained by a treatment of the boronic ester with SOCl2 and imidazole in the presence of borosilicate glass (the catalyst); this complex was hydrolized in aq. CH3CN; | 82% |
phenylboronic acid
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 8h; | 81% |
Trimethyl borate
phenylmagnesium bromide
A
phenol
B
phenylboronic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at -12℃; Temperature; Concentration; Flow reactor; | A 7.9% B 80.7% |
Conditions | Yield |
---|---|
Stage #1: iodobenzene With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages; | 80% |
Multi-step reaction with 2 steps 2: H2O View Scheme |
Trimethyl borate
phenylmagnesium bromide
A
chlorobenzene
B
phenol
C
phenylboronic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at 22℃; Temperature; Concentration; Flow reactor; | A 8.9% B 5.7% C 79.6% |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at -10℃; Inert atmosphere; | 76% |
borane
phenylboronic acid
Conditions | Yield |
---|---|
With water; phenylmagnesium bromide In tetrahydrofuran slow addn. of 10 mmol of the Grignard reagent to a stirred soln. of borane in THF (40 mmol); the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;; | 75% |
With bromobenzene; water; magnesium In tetrahydrofuran a 2.0 M soln. of borane (40 mmol) in THF was added to flame dried Mg turnings (12 mmol) at 0°C; slow addn. of the aryl bromide (10 mmol)in THF; stirring at room temp. for 12-16 h; the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;; |
Phenyl triflate
phenylboronic acid
Conditions | Yield |
---|---|
Stage #1: Phenyl triflate With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages; | 74% |
Conditions | Yield |
---|---|
at 80℃; for 1h; | 100% |
for 0.166667h; Schlenk technique; | 96% |
In dichloromethane; ethyl acetate at 20℃; | 81% |
1,2-diamino-benzene
phenylboronic acid
2-phenyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
Conditions | Yield |
---|---|
at 40℃; for 1h; | 100% |
In toluene for 2h; Reflux; | 92% |
In toluene stirring mixt. of diamine deriv. and phenylboric acid in toluene for 2 hat reflux; filtration, washing with petroleum ether, NMR; | 92% |
2-hydroxyresorcinol
phenylboronic acid
2-phenyl-1,3,2-benzodioxaborole-4-ol
Conditions | Yield |
---|---|
at 40℃; for 2h; | 100% |
mannitol
phenylboronic acid
(2R,3R,4R,5R)-1:2,3:4,5:6-O1:O2,O3:O4,O5:O6-tris(phenylboranato)-D-mannitol
Conditions | Yield |
---|---|
at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
at 110℃; for 6h; | 100% |
at 110℃; for 6h; Inert atmosphere; Neat (no solvent); | 100% |
Stage #1: phenylboronic acid With barium(II) hydroxide In water at 80℃; for 0.0833333h; Stage #2: With Au38(SCH2CH2Ph)24 In toluene at 80℃; for 12h; Reagent/catalyst; | 100% |
anthranilic acid
phenylboronic acid
2-phenyl-1,2-dihydro-benzo[a][1,3,2]-oxazaborinin-4-one
Conditions | Yield |
---|---|
at 20℃; for 1h; | 100% |
In toluene for 16h; Inert atmosphere; Dean-Stark; Reflux; | 93% |
In toluene | |
In tetrahydrofuran for 24h; Reflux; | 72 %Spectr. |
2,2-Dimethyl-1,3-propanediol
phenylboronic acid
5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane
Conditions | Yield |
---|---|
With magnesium sulfate In diethyl ether at 25℃; for 20h; Inert atmosphere; | 100% |
In tetrahydrofuran for 0.666667h; Inert atmosphere; Dean-Stark; Reflux; | 100% |
With magnesium sulfate In diethyl ether at 20℃; for 20h; | 100% |
Conditions | Yield |
---|---|
100% | |
In di-isopropyl ether |
naphthalene-1,8-diamine
phenylboronic acid
2-phenyl-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
Conditions | Yield |
---|---|
at 0℃; for 1h; | 100% |
With 1H-imidazole; iron(III) chloride In water; acetonitrile at 20℃; for 2h; Catalytic behavior; Temperature; Time; Inert atmosphere; | 93% |
at 150℃; for 0.25h; Microwave irradiation; Sealed tube; | 90% |
oxalodihydrazonic acid dianilide
phenylboronic acid
Conditions | Yield |
---|---|
100% | |
In di-isopropyl ether |
Conditions | Yield |
---|---|
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In tert-Amyl alcohol for 12h; Solvent; Suzuki-Miyaura Coupling; Heating; | 100% |
With cesiumhydroxide monohydrate; 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl; palladium diacetate In water; butan-1-ol at 25℃; for 0.25h; Solvent; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere; | 100% |
With potassium phosphate; catacxium A; palladium diacetate In toluene at 100℃; for 20h; Suzuki reaction; | 99% |
Conditions | Yield |
---|---|
With [Pd(N-(naphthyl)-salicylaldimine(-2H))(triphenylphosphine)]; sodium hydroxide at 120℃; for 24h; Reagent/catalyst; Suzuki Coupling; | 100% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux; | 100% |
With potassium phosphate; (PdCl2)(2-pyridyl)-6-isopropyl cis piperidine complex In water; N,N-dimethyl-formamide at 110℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; tricyclohexylphosphine; dichloro bis(acetonitrile) palladium(II) at 85 - 90℃; for 5h; Suzuki-Miyaura reaction; | 100% |
With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling; | 99% |
With 2-((3-sulfonatomesityl)-5-sulfonatoindenyl)dicyclohexylphosphinehydrate sodium salt; palladium diacetate; potassium carbonate In water at 100℃; for 24h; Suzuki-Miyaura Coupling; | 95% |
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 6h; Suzuki-Miyaura cross-coupling reaction; | 100% |
With potassium carbonate In ethanol; water at 30℃; for 1h; Suzuki-Miyaura Coupling; | 100% |
With N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate; palladium dichloride In 1,4-dioxane; N,N-dimethyl-formamide at 90℃; for 6h; Suzuki coupling; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With Cs2O3; PCy3 adduct of cyclopalladated ferrocenylimine In 1,4-dioxane at 100℃; for 15h; Suzuki cross-coupling reaction; | 100% |
With dichloro(cycloocta-1,5-diene)palladium (II); 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); potassium carbonate In methanol for 0.166667h; Suzuki cross-coupling reaction; Microwave irradiation; Inert atmosphere; | 100% |
With potassium carbonate In methanol at 100℃; for 0.0833333h; Suzuki-Miyaura Coupling; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With potassium phosphate monohydrate; 4,4'-di-tBu-2,2'-dipyridylpalladium(II) dichloride In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling; | 100% |
With potassium carbonate; palladium dichloride In water at 20 - 90℃; Suzuki coupling; Inert atmosphere; | 99% |
With potassium carbonate In water at 90℃; for 0.25h; Suzuki reaction; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With trans-dibromobis(1-butyl-3-methylimidazol-2-ylidene)palladium(II); sodium hydrogencarbonate In ethylene glycol at 110℃; for 1h; Catalytic behavior; Suzuki-Miyaura Coupling; Schlenk technique; | 100% |
With tetrabutylammomium bromide; sodium carbonate In water at 100℃; for 2h; Suzuki coupling; | 99% |
With sodium carbonate In 1,2-dimethoxyethane; water for 16h; Heating / reflux; | 86% |
Conditions | Yield |
---|---|
With potassium carbonate; copper-palladium In N,N-dimethyl-formamide at 110℃; for 4h; Suzuki cross-coupling; | 100% |
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation; | 97% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100 - 102℃; Suzuki Coupling; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With sodium hydroxide; palladium dichloride In water for 0.166667h; Product distribution; Ambient temperature; other reagents, reaction times; | 100% |
With sodium hydroxide; palladium diacetate In water at 20℃; for 2h; Suzuki reaction; | 100% |
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 80℃; for 36h; Suzuki-Miyaura Coupling; Inert atmosphere; | 100% |
With C28H38Cl2N2O6PdS2(2-)*2Na(1+); tetrabutylammomium bromide; potassium carbonate In water at 75℃; Suzuki coupling; Inert atmosphere; | 99% |
With Br(1-)*C28H29BrN5O2Pd(1+); potassium carbonate In methanol; water at 100℃; for 3h; Suzuki-Miyaura coupling; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 13h; Suzuki-Miyaura cross-coupling reaction; | 100% |
With potassium phosphate; triphenylphosphine; Ni(II) complexes of bidentate carbene; phosphine ligand In toluene at 80℃; Suzuki cross-coupling; | 100% |
With [PdCl2(2-ethyl-2-oxazoline)2]; potassium carbonate In toluene at 110℃; for 3h; Suzuki reaction; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 14h; Suzuki-Miyaura cross-coupling reaction; | 100% |
With 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling; | 100% |
With 1,4-diaza-bicyclo[2.2.2]octane; PEG-400; potassium carbonate; palladium diacetate at 110℃; for 2h; Suzuki-Miyaura cross-coupling reaction; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; copper-palladium In N,N-dimethyl-formamide at 110℃; Kinetics; Product distribution; Further Variations:; Catalysts; Reaction partners; Suzuki cross-coupling; | 100% |
With sodium hydroxide; Pd-dodecanethiolate nanoparticles In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura cross-coupling; | 100% |
With sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate; 2C10H15N2(1+)*Cl4Pd(2-) In water at 110℃; for 12h; Conversion of starting material; Suzuki Coupling; | 100% |
Conditions | Yield |
---|---|
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water at 50℃; for 24h; Solvent; Temperature; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox; | 100% |
With di-tert-butyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water at 50℃; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere; Glovebox; | 100% |
With sodium carbonate In water at 100℃; Suzuki-Miyaura reaction; | 99.1% |
Conditions | Yield |
---|---|
With potassium phosphate; (η5-C5H5)Re(NO)(P(C6H5)3)(C(CH3)3)2; palladium diacetate In toluene at 100℃; for 1h; Suzuki cross-couplings reaction; | 100% |
With N,N-dicyclohexyl-2-(dicyclohexylphosphanyl)benzenesulfonamide; tris(dibenzylideneacetone)dipalladium (0); caesium carbonate In 1,4-dioxane at 80℃; for 3h; Suzuki-Miyaura cross coupling; | 100% |
With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 80℃; for 12h; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; Suzuki cross-coupling; | 100% |
Conditions | Yield |
---|---|
With [Pd(1-butylimidazole)2Cl2]; potassium hydroxide In water; isopropyl alcohol at 40℃; for 1h; Suzuki-Miyaura reaction; Under air; | 100% |
With caesium carbonate In water; isopropyl alcohol at 80℃; for 3h; Suzuki-Miyaura reaction; Inert atmosphere; | 100% |
With potassium hydroxide In propan-1-ol; water at 60℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
With C31H26N6O4Pd; potassium carbonate In water at 100℃; for 3h; Suzuki-Miyaura coupling; | 100% |
With potassium phosphate; 1,1'-bis(4-methoxyphenyl)-3,3'-methylene-diimidazoline-2,2'-diylidene-palladium(II)-dibromide In toluene at 40℃; for 2h; Reagent/catalyst; Temperature; Time; Suzuki-Miyaura Coupling; Inert atmosphere; | 100% |
With C16H21ClN2Pd; sodium carbonate In methanol at 85℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling; | 100% |
2-Bromo-6-methoxynaphthalene
phenylboronic acid
2-methoxy-6-phenylnaphthalene
Conditions | Yield |
---|---|
With potassium phosphate; (η5-C5H5)Re(NO)(P(C6H5)3)P(C6H5)2; palladium diacetate In toluene at 100℃; for 0.25h; Suzuki cross-couplings reaction; | 100% |
With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In water at 70℃; for 1h; | 99% |
With potassium fluoride; o-(dicyclohexylphosphino)diisopropylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 80℃; for 40h; Suzuki cross-coupling; | 98% |
4-methoxycarbonylphenyl bromide
phenylboronic acid
methyl 4-phenylbenzoate
Conditions | Yield |
---|---|
With potassium phosphate; second generation phosphine dendrimer-stabilized palladium In 1,4-dioxane for 20h; Suzuki coupling; Heating; | 100% |
With potassium phosphate; silica gel; palladium In toluene at 110℃; for 5h; Suzuki-Miyaura reaction; | 100% |
With potassium phosphate tribasic heptahydrate In 1,4-dioxane for 20h; Suzuki coupling; Reflux; | 100% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate; palladium diacetate In acetone at 110℃; for 2h; Suzuki-Miyaura cross-coupling reaction; | 100% |
With sodium hydroxide; Pd-dodecanethiolate nanoparticles In tetrahydrofuran at 20℃; for 17h; Suzuki-Miyaura cross-coupling; | 100% |
With caesium carbonate; (1-adamantylisonitrile)2PdCl2 In 1,4-dioxane for 18h; Product distribution; Further Variations:; Catalysts; Suzuki-Miyaura reaction; Heating; | 100% |
Phenylboronic acid is white powder and is commonly used in organic synthesis. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis. With the CAS NO.98-80-6, Phenylboronic acid is soluble in most polar organic solvents and is poorly soluble in hexanes and carbon tetrachloride. And it is also named as benzeneboronic acid.
Physical properties about Phenylboronic acid are: (1)ACD/LogP: 1.237; (2)ACD/LogD (pH 5.5): 1.24; (3)ACD/LogD (pH 7.4): 1.21; (4)ACD/BCF (pH 5.5): 5.12; (5)ACD/BCF (pH 7.4): 4.77; (6)ACD/KOC (pH 5.5): 112.04; (7)ACD/KOC (pH 7.4): 104.39; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.534; (12)Molar Refractivity: 33.288 cm3; (13)Molar Volume: 107.063 cm3; (14)Polarizability: 13.197 10-24cm3; (15)Surface Tension: 41.4830017089844 dyne/cm; (16)Density: 1.139 g/cm3; (17)Flash Point: 114.586 °C; (18)Enthalpy of Vaporization: 53.224 kJ/mol; (19)Boiling Point: 265.856 °C at 760 mmHg; (20)Vapour Pressure: 0.00400000018998981 mmHg at 25°C
Preparation of Phenylboronic acid: There are numerous methods to synthesize phenylboronic acid. One of the most common synthesis uses phenylmagnesium bromide and trimethyl borate to form the ester PhB(OMe)2, which is then hydrolyzed to the product.
PhMgBr + B(OMe)3 → PhB(OMe)2 + MeOMgBr
PhB(OMe)2 + H2O → PhB(OH)2 + MeOH
Uses of Phenylboronic acid: Phenylboronic acid is used in numerous cross coupling reactions. Phenylboronic acid is also used in biology schemes as receptors and sensors for carbohydrates, antimicrobial agents and enzyme inhibitors, neutron capture therapy for cancer, transmembrane transport, and bioconjugation and labeling of proteins and cell surface.
When you are using this chemical, please be cautious about it as the following:
1. Do not breathe dust;
2. Avoid contact with skin and eyes;
3. Wear suitable protective clothing, gloves and eye/face protection;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H;
(2)InChIKey=HXITXNWTGFUOAU-UHFFFAOYSA-N;
(3)Smilesc1c(cccc1)B(O)O
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 450mg/kg (450mg/kg) | Bulletin de l'Academie Nationale de Medicine Vol. 135, Pg. 314, 1951. | |
guinea pig | LDLo | intraperitoneal | 284mg/kg (284mg/kg) | Bulletin de l'Academie Nationale de Medicine Vol. 135, Pg. 314, 1951. | |
mouse | LD50 | intraperitoneal | 500mg/kg (500mg/kg) | National Technical Information Service. Vol. AD277-689, | |
mouse | LD50 | intravenous | 221mg/kg (221mg/kg) | Acta Physiologica Polonica. Vol. 12, Pg. 173, 1961. | |
rabbit | LDLo | oral | 600mg/kg (600mg/kg) | "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964. | |
rabbit | LDLo | skin | 4500mg/kg (4500mg/kg) | "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964. | |
rat | LD50 | oral | 740mg/kg (740mg/kg) | "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964. |
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