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5720-07-0

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5720-07-0 Usage

Chemical Properties

white to light beige crystalline powder

Uses

Different sources of media describe the Uses of 5720-07-0 differently. You can refer to the following data:
1. 4-Methoxyphenylboronic acid can be used as a common organic reagent in Suzuki coupling reactions to study the N-arylation of imidazoles and amines catalyzed by copper exchange of calcium fluorophosphates.Reagent used in the preparation of various biological inhibitors.
2. 4-Methoxyphenylboronic acid is a reagent used forSuzuki-Miyaura cross-coupling reactionsPd-catalyzed direct arylationHighly effective synthesis using palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in waterPalladium-catalyzed stereoselective Heck-type reactionTandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequenceCopper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides Ruthenium catalyzed direct arylationRh-catalyzed asymmetric conjugate addition
3. 4-Methoxylphenylboronic Acid is a phenylboronic acid used to investigate boron function in plants.
4. suzuki reaction

Check Digit Verification of cas no

The CAS Registry Mumber 5720-07-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,2 and 0 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 5720-07:
(6*5)+(5*7)+(4*2)+(3*0)+(2*0)+(1*7)=80
80 % 10 = 0
So 5720-07-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H9BO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3

5720-07-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (M1252)  4-Methoxyphenylboronic Acid (contains varying amounts of Anhydride)  

  • 5720-07-0

  • 5g

  • 180.00CNY

  • Detail
  • TCI America

  • (M1252)  4-Methoxyphenylboronic Acid (contains varying amounts of Anhydride)  

  • 5720-07-0

  • 25g

  • 580.00CNY

  • Detail
  • Alfa Aesar

  • (A14462)  4-Methoxybenzeneboronic acid, 97+%   

  • 5720-07-0

  • 1g

  • 146.0CNY

  • Detail
  • Alfa Aesar

  • (A14462)  4-Methoxybenzeneboronic acid, 97+%   

  • 5720-07-0

  • 5g

  • 483.0CNY

  • Detail
  • Alfa Aesar

  • (A14462)  4-Methoxybenzeneboronic acid, 97+%   

  • 5720-07-0

  • 25g

  • 2181.0CNY

  • Detail

5720-07-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methoxyphenylboronic acid

1.2 Other means of identification

Product number -
Other names para-methoxyphenylboronic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5720-07-0 SDS

5720-07-0Synthetic route

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
171364-79-7

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride; polystyrene boronic acid In acetonitrile at 20℃; for 18h;99%
Stage #1: 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With potassium hydrogen difluoride In methanol at 20℃; for 0.25h;
Stage #2: With lithium hydroxide In acetonitrile at 20℃; for 20h;
95%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With iodine; magnesium In tetrahydrofuran at 20 - 80℃;
Stage #2: With Trimethyl borate In tetrahydrofuran at -10 - 20℃;
97%
Stage #1: 1-bromo-4-methoxy-benzene With diisobutylaluminium hydride; magnesium; lithium chloride In tetrahydrofuran; toluene at 20℃; for 15h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
92%
Stage #1: 1-bromo-4-methoxy-benzene With magnesium In tetrahydrofuran
Stage #2: With Trimethyl borate In tetrahydrofuran for 6h; Acidic conditions;
91%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Trimethyl borate
121-43-7

Trimethyl borate

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With Mg In tetrahydrofuran Mg (reflux), THF, B(OCH)3, bromobenzene-compound (-10°C) or n-butyllithium, B(OCH3)3, -78°C, THF;97%
Stage #1: 1-bromo-4-methoxy-benzene With magnesium In tetrahydrofuran
Stage #2: Trimethyl borate In tetrahydrofuran; diethyl ether at -70 - 20℃;
95%
With magnesium In tetrahydrofuran; diethyl ether aryl bromide soln. dropped to Mg in THF, filtered, Grignard soln. added dropwise to soln. of calcd. amt. of B compd. in Et2O at -70°C, warming to room temp. overnight; mixt. added to ice cold and concd. aq. H2SO4, stirred for 30 min, extd. with ether (repeatedly), dried with Na2SO4, evapn., dried in vac., elem.anal.;95%
hydrogenchloride
7647-01-0

hydrogenchloride

Pt(OB(C6H4OMe-4)OB(C6H4OMe-4)O)(dppe)
883153-46-6

Pt(OB(C6H4OMe-4)OB(C6H4OMe-4)O)(dppe)

[platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)]
83095-83-4, 14647-25-7

[platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)]

B

2,4,6-tris(4-methoxyphenyl)boroxine
7294-51-1

2,4,6-tris(4-methoxyphenyl)boroxine

C

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran under N2 or Ar; to a THF soln. of Pt-contg. compd. (0.05 mmol) was addedHCl (0.1 mmol); stirring at room temp. for 2 h; addn. of hexane; the complex was filtered off and dried under vac.; elem. anal.;A 97%
B n/a
C n/a
4-methoxyphenyl magnesium bromide
13139-86-1

4-methoxyphenyl magnesium bromide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-methoxyphenyl magnesium bromide With Trimethyl borate In tetrahydrofuran at 20℃;
Stage #2: With acidic aq. solution
96%
Stage #1: 4-methoxyphenyl magnesium bromide With Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #2: With hydrogenchloride In water
71%
Stage #1: 4-methoxyphenyl magnesium bromide With Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran Further stages.;
4.37 g
With Trimethyl borate at -78℃; for 8h;
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
96%
Stage #1: 4-chloromethoxybenzene With tetrahydroxydiboron; ethanol; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[(2-(2-aminoethyl)phenyl)]palladium(II); potassium acetate; sodium t-butanolate; XPhos at 80℃; for 18h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In ethyl acetate for 0.5h; Inert atmosphere;
82%
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos In ethanol at 80℃; for 2h; Inert atmosphere;
With methanol; tetrakis(dimethylamido)diborane; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; XPhos at 20 - 60℃; for 5.0833h; Inert atmosphere; Sealed tube;
potassium 4-(methoxy)phenyltrifluoroborate

potassium 4-(methoxy)phenyltrifluoroborate

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With aluminum oxide; water at 70℃; for 0.25h; Microwave irradiation;93%
With water; silica gel at 20℃; for 1h; Inert atmosphere;83%
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 0.5h;81%
With water In tetrahydrofuran at 55℃; Kinetics; Reagent/catalyst;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran; methanol at 50℃; for 1h; Catalytic behavior; Reagent/catalyst; Concentration; Time; Inert atmosphere;92%
In methanol at 15℃; for 3h; Microwave irradiation;87%
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); tetramethyl ammonium acetate In 2-methyltetrahydrofuran; methanol; water at 40℃; for 8h; Schlenk technique; Inert atmosphere;70%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Triisopropyl borate
5419-55-6

Triisopropyl borate

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃;
91%
With magnesium; iodine; hydrochloric acid In tetrahydrofuran; diethyl ether Mg and I2 heated under Ar, diethyl ether and soln. of 4-bromoanisole added, mixt. warmed to 40°C for 30 min, soln. transferred into soln.of (iso-PrO)3B in THF at -78°C, stirred overnight, warmed to roo m temp., HCl added, stirred for 1 h; extn. (aq. NH4Cl/NaOH and EtOAc), drying (MgSO4), evapn.;20%
With n-butyllithium In tetrahydrofuran; hexane
Pt(OB(C6H4OMe-4)OB(C6H4OMe-4)O)(dppe)
883153-46-6

Pt(OB(C6H4OMe-4)OB(C6H4OMe-4)O)(dppe)

trifluoroacetic acid
76-05-1

trifluoroacetic acid

Pt(CF3CO2)2(dppe)
69005-06-7

Pt(CF3CO2)2(dppe)

B

2,4,6-tris(4-methoxyphenyl)boroxine
7294-51-1

2,4,6-tris(4-methoxyphenyl)boroxine

C

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran under N2 or Ar; to a THF soln. of Pt-contg. compd. (0.05 mmol) was addedCF3COOH (0.1 mmol); stirring at room temp. for 2 h; addn. of hexane; the complex was filtered off and dried under vac.; elem. anal.;A 91%
B n/a
C n/a
methanol
67-56-1

methanol

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

dicyclohexylamine borane complex
131765-96-3

dicyclohexylamine borane complex

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene; dicyclohexylamine borane complex With magnesium In tetrahydrofuran at 70℃;
Stage #2: methanol In tetrahydrofuran at 0℃; for 1h;
Stage #3: With hydrogenchloride; water In methanol at 20℃; for 1h;
91%
water
7732-18-5

water

potassium 4-(methoxy)phenyltrifluoroborate

potassium 4-(methoxy)phenyltrifluoroborate

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With montmorillonite K10 at 25℃; for 1.5h;90%
With 1H-imidazole; iron(III) chloride at 20℃; for 0.25h; Inert atmosphere;81%
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;
para-iodoanisole
696-62-8

para-iodoanisole

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: para-iodoanisole 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;
89%
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos In ethanol at 80℃; for 1h; Inert atmosphere;
(p-methoxyphenyl)tri-n-butylstannane
70744-47-7

(p-methoxyphenyl)tri-n-butylstannane

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With borane; water In tetrahydrofuran for 1h; Heating;88%
4-methoxyphenyl triflate
66107-29-7

4-methoxyphenyl triflate

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-methoxyphenyl 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;
87%
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos In ethanol at 80℃; for 2h; Inert atmosphere;
With methanol; tetrakis(dimethylamido)diborane; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; XPhos at 20 - 60℃; for 6.5833h; Inert atmosphere; Sealed tube;
methanol
67-56-1

methanol

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

diisopropylamine borane
55124-35-1

diisopropylamine borane

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 1-bromo-4-methoxy-benzene In tetrahydrofuran at 70℃;
Stage #3: methanol Reagent/catalyst; Further stages;
87%
triethyl borate
150-46-9

triethyl borate

p-methoxyphenyllithium
14774-77-7

p-methoxyphenyllithium

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran addn. of B-compd. to org. compd. in THF, stirring (-78°C, 1.5 h); addn. of satd. soln. of aq. NH4Cl (-78°C), warming (room temp.),DDN: OF H2O, shaking with ether, washing of ether extracts (satd. aq. NaHCO3 and satd. brine), drying (Na2SO4), filtration, evapn. (vac.), crystn. (H2O);86%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-methoxy-aniline With hydrogenchloride; sodium nitrite In methanol; water at 0 - 5℃; for 0.5h;
Stage #2: With tetrahydroxydiboron In methanol; water at 20℃; for 1h;
86%
Multi-step reaction with 2 steps
1.1: water / 0.03 h / 20 °C
1.2: 0.25 h / 0 °C
2.1: N,N-dimethyl-formamide / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: tetrafluoroboric acid; sodium nitrite / water / 1 h / 0 °C
1.2: 0 - 20 °C
2.1: methanol / 17 h / 20 °C / Irradiation; Inert atmosphere; Schlenk technique
View Scheme
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

water
7732-18-5

water

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In ethanol mixt. B2(OH)4, hexane wash, Pd-complex, (iPr)3C6H2C6H4-2-P(cyclo-C6H11),NaOBu-t and excess KOAc in EtOH at 80°C for 18 h;82%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-methoxy-N,N,N-trimethylbenzenaminium iodide
17310-99-5

4-methoxy-N,N,N-trimethylbenzenaminium iodide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;82%
2,5-bis-(4-methoxyphenyl)-4,4-dimethyl-[1,3,2]dioxaborolane

2,5-bis-(4-methoxyphenyl)-4,4-dimethyl-[1,3,2]dioxaborolane

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 24h;80%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-methoxy-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;
77%
Stage #1: 4-methoxy-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: tetrahydroxydiboron With potassium carbonate In water at 20℃; for 0.333333h; Reagent/catalyst; Solvent;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Trimethyl borate
121-43-7

Trimethyl borate

water
7732-18-5

water

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With magnesium In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 4h; Inert atmosphere;
Stage #3: water With hydrogenchloride
77%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Trimethyl borate
121-43-7

Trimethyl borate

sulfuric acid
7664-93-9

sulfuric acid

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With magnesium In tetrahydrofuran74%
borane
13283-31-3

borane

4-methoxyphenyl magnesium bromide
13139-86-1

4-methoxyphenyl magnesium bromide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With water 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;;73%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

diisopropylamine borane
55124-35-1

diisopropylamine borane

para-bromotoluene
106-38-7

para-bromotoluene

water
7732-18-5

water

A

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

B

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

C

B-(4-methoxyphenyl)-B-(4-methylphenyl)borinic acid

B-(4-methoxyphenyl)-B-(4-methylphenyl)borinic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane; para-bromotoluene With magnesium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: 1-bromo-4-methoxy-benzene In tetrahydrofuran at 40℃; for 14h; Inert atmosphere;
Stage #3: water In tetrahydrofuran Temperature; Inert atmosphere;
A 9%
B 12%
C 73%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

para-iodoanisole
696-62-8

para-iodoanisole

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

Conditions
ConditionsYield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); tetramethyl ammonium acetate In 2-methyltetrahydrofuran; methanol; water at 40℃; for 6.5h; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere;70%
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tributyl-amine; water In acetonitrile at 25℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;40%
In methanol; water at -5℃; for 0.166667h; UV-irradiation; Flow reactor; chemoselective reaction;100 %Spectr.
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;
o-iodo-methyl-benzoic acid
610-97-9

o-iodo-methyl-benzoic acid

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

methyl 4'-methoxybiphenyl-2-carboxylate
17103-25-2

methyl 4'-methoxybiphenyl-2-carboxylate

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate In water; acetonitrile at 60℃; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With bis(triphenylphosphine)palladium(II) dichloride; sodium carbonate In tetrahydrofuran; water at 80℃; for 14h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube;95%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In toluene for 18h; Heating;80%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.166667h;100%
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h;96%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;85%
bromobenzene
108-86-1

bromobenzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; p-tolylboronic pinacol ester In 1,4-dioxane; water at 70℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; chemoselective reaction;100%
With potassium carbonate In ethanol; water at 50℃; for 0.5h; Catalytic behavior; Suzuki-Miyaura Coupling;100%
With potassium carbonate; palladium dichloride In pyridine for 4h; Suzuki cross-coupling; Heating;99%
iodobenzene
591-50-4

iodobenzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With sodium carbonate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;100%
With SIPr-PdCl2-Py; sodium t-butanolate In tetrahydrofuran at 70℃; for 12h; Suzuki-Miyaura Coupling;100%
With caesium carbonate; 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide In N,N-dimethyl-formamide at 125 - 130℃; for 19h; Suzuki-Miyaura cross-coupling reaction;99%
para-chlorotoluene
106-43-4

para-chlorotoluene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-(4-tolyl)anisole
53040-92-9

4-(4-tolyl)anisole

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 3-butyl-1-methyl-5-[9-(3-methyl-1H-imidazol-3-ium-1-yl)nonyl]-3H-1,2,3-triazol-1-ium diiodide; caesium carbonate In 1,4-dioxane Suzuki-Miyaura reaction; Inert atmosphere; Heating;100%
With tris(dibenzylideneacetone)dipalladium (0); C3H3N2(C9H11)2*HCl; caesium carbonate In 1,4-dioxane at 80℃; for 1.5h;99%
Stage #1: 4-methoxyphenylboronic acid With allyl(1,3-bis(2,6-diisopropyl-4-(3-((3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy)propyl)phenyl)-imidazol-2-ylidene)palladium(II) chloride; potassium tert-butylate In ethanol at 30℃; for 0.5h; Inert atmosphere;
Stage #2: para-chlorotoluene In ethanol at 30℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere;
99%
4-tolyl iodide
624-31-7

4-tolyl iodide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-(4-tolyl)anisole
53040-92-9

4-(4-tolyl)anisole

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 80℃; for 0.166667h; Suzuki Coupling;100%
With sodium carbonate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;100%
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-(4'-methoxyphenyl)benzaldehyde
52988-34-8

4-(4'-methoxyphenyl)benzaldehyde

Conditions
ConditionsYield
With sodium carbonate In ethanol at 75℃; for 2h; Suzuki-Miyaura cross coupling;100%
With palladium 10% on activated carbon; caesium carbonate at 100℃; for 24h; Suzuki-Miyaura coupling; Neat (no solvent);100%
With potassium tert-butylate In ethanol; water at 25℃; for 2h; Suzuki-Miyaura Coupling;100%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

N,N-dimethyl 2-iodo-3-(trans-2-methoxycarbonylethenyl)-4-trimethylsilyl-1H-pyrrole-1-sulfonamide
284663-47-4

N,N-dimethyl 2-iodo-3-(trans-2-methoxycarbonylethenyl)-4-trimethylsilyl-1H-pyrrole-1-sulfonamide

N,N-dimethyl 2-(p-methoxyphenyl)-3-(trans-2-methoxycarbonylethenyl)-4-trimethylsilyl-1H-pyrrole-1-sulfonamide
284663-48-5

N,N-dimethyl 2-(p-methoxyphenyl)-3-(trans-2-methoxycarbonylethenyl)-4-trimethylsilyl-1H-pyrrole-1-sulfonamide

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium sulfate In methanol; toluene at 90 - 100℃; for 2h; Phenylation;100%
para-bromotoluene
106-38-7

para-bromotoluene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-(4-tolyl)anisole
53040-92-9

4-(4-tolyl)anisole

Conditions
ConditionsYield
With potassium carbonate; palladium dichloride In pyridine for 4h; Suzuki cross-coupling; Heating;100%
With C21H26Cl2N2Pd; potassium carbonate In toluene at 110℃; for 18h; Suzuki Coupling; Inert atmosphere; Sealed tube;100%
With tetrabutylammomium bromide; sodium carbonate; palladium contaminants present in sodium carbonate In water at 150℃; for 0.0833333h; Suzuki coupling; microwave irradiation;99%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4'-methoxy-2-methylbiphenyl
92495-54-0

4'-methoxy-2-methylbiphenyl

Conditions
ConditionsYield
With potassium phosphate; palladium-incarcerated polystyrene-based copolymer; tris(o-methoxyphenyl)phosphine In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;100%
With potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 20℃; for 6h; Suzuki cross-coupling;98%
With potassium fluoride; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 2h; Suzuki cross-coupling;98%
p-tolyl triflate
29540-83-8

p-tolyl triflate

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-(4-tolyl)anisole
53040-92-9

4-(4-tolyl)anisole

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 3-butyl-1-methyl-5-[9-(3-methyl-1H-imidazol-3-ium-1-yl)nonyl]-3H-1,2,3-triazol-1-ium diiodide; caesium carbonate In 1,4-dioxane Suzuki-Miyaura reaction; Inert atmosphere; Heating;100%
With potassium fluoride; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 20℃; for 4h; Suzuki cross-coupling;95%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

para-bromoacetophenone
99-90-1

para-bromoacetophenone

1-(4'-methoxy-biphenyl-4-yl)-ethanone
13021-18-6

1-(4'-methoxy-biphenyl-4-yl)-ethanone

Conditions
ConditionsYield
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 2h; Suzuki-Miyaura reaction;100%
With potassium carbonate In water at 80℃; for 5h; Suzuki Coupling;100%
With potassium carbonate In methanol at 25℃; for 1h; Wavelength; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation;100%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

4-(4-methoxyphenyl)aniline
1137-77-5

4-(4-methoxyphenyl)aniline

Conditions
ConditionsYield
With sodium carbonate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;100%
With potassium carbonate In ethanol at 78℃; for 1h; Suzuki-Miyaura coupling; Air atmosphere;96%
With potassium carbonate In methanol; water at 40 - 45℃; for 1.5h; Suzuki Coupling;92%
3-Bromopyridine
626-55-1

3-Bromopyridine

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

3-(4-methoxyphenyl)pyridine
5958-02-1

3-(4-methoxyphenyl)pyridine

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 120℃; for 5h; Suzuki Coupling;100%
With potassium carbonate In isopropyl alcohol at 85 - 90℃; for 24h; Suzuki-Miyaura Coupling;99%
With sodium phosphate; palladium on activated charcoal In isopropyl alcohol at 80℃; for 6h; Suzuki-Miyaura coupling reaction;98%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

5-chloro-4-methoxy-2-methyl-2H-pyridazin-3-one
77541-59-4

5-chloro-4-methoxy-2-methyl-2H-pyridazin-3-one

4-methoxy-5-(4-methoxyphenyl)-2-methyl-3(2H)-pyridazinone
335349-24-1

4-methoxy-5-(4-methoxyphenyl)-2-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; Suzuki cross-coupling;100%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

5-chloro-4-methoxy-2-phenyl-3(2H)-pyridazinone
76929-42-5

5-chloro-4-methoxy-2-phenyl-3(2H)-pyridazinone

4-methoxy-5-(4-methoxyphenyl)-2-phenyl-3(2H)-pyridazinone
335349-29-6

4-methoxy-5-(4-methoxyphenyl)-2-phenyl-3(2H)-pyridazinone

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; Suzuki cross-coupling;100%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-methoxy-phenol
150-76-5

4-methoxy-phenol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 8h; Reagent/catalyst; Irradiation; Sonication;100%
With solid poly(N-vinylpyrrolidone)-hydrogen peroxide complex (PVD-H2O2 complex) In dichloromethane at 20℃; regioselective reaction;99%
With menadione; sodium hydrogencarbonate; sodium L-ascorbate In ethanol; water at 20℃; under 760.051 Torr; for 24h; pH=8.5; Darkness; Green chemistry;99%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-chloro-5-methoxy-2-methyl-2H-pyridazin-3-one
14628-57-0

4-chloro-5-methoxy-2-methyl-2H-pyridazin-3-one

5-methoxy-4-(4-methoxyphenyl)-2-methyl-3(2H)-pyridazinone

5-methoxy-4-(4-methoxyphenyl)-2-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; Suzuki cross-coupling;100%
4-(trifluormethanesulfonyloxy)benzaldehyde
17763-69-8

4-(trifluormethanesulfonyloxy)benzaldehyde

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-(4'-methoxyphenyl)benzaldehyde
52988-34-8

4-(4'-methoxyphenyl)benzaldehyde

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride In ethanol; toluene Suzuki coupling; Heating;100%
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 12h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;78%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4,4'-Dimethoxybiphenyl
2132-80-1

4,4'-Dimethoxybiphenyl

Conditions
ConditionsYield
With air; potassium carbonate; [Pd(Cl)κ2N,C,-CH2C6H2(4,6-Me)2CH=NC6H3(2,6-iPr)2]2 In ethanol for 2h; Suzuki-Miyaura coupling reaction; Heating;100%
With sodium carbonate; palladium on activated charcoal In ethanol at 20℃; for 5h; Suzuki-Miyaura cross-coupling;100%
With potassium carbonate In water at 50℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;100%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

2,3-bis(4-methoxyphenyl)naphthalene-1,4-dione
50982-55-3

2,3-bis(4-methoxyphenyl)naphthalene-1,4-dione

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; benzene for 4h; Suzuki coupling; Heating;100%
para-iodoanisole
696-62-8

para-iodoanisole

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4,4'-Dimethoxybiphenyl
2132-80-1

4,4'-Dimethoxybiphenyl

Conditions
ConditionsYield
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 In water at 80℃; for 2h; Suzuki Coupling;100%
With sodium carbonate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;100%
p-trifluoromethylphenyl bromide
402-43-7

p-trifluoromethylphenyl bromide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

1-(4-methoxyphenyl)-4-(trifluoromethyl)benzene
10355-12-1

1-(4-methoxyphenyl)-4-(trifluoromethyl)benzene

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 120℃; for 5h; Suzuki Coupling;100%
With sodium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; palladium diacetate In water at 60℃; for 1h; Suzuki coupling;99%
With potassium phosphate; [5-(3-butylbenzimidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxy calix[4]arene] (pyridine) palladium(II) dibromide In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;99%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-chloro-6-iodo-quinoline
40107-07-1

4-chloro-6-iodo-quinoline

4-chloro-6-(4-methoxyphenyl)quinoline
500127-41-3

4-chloro-6-(4-methoxyphenyl)quinoline

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 64℃; for 15h; Product distribution; Further Variations:; Catalysts; Reaction partners; Reagents; Solvents; temperatures, reaction times; Suzuki reaction;100%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 15h; Product distribution; Further Variations:; Catalysts; Heating;100%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-methoxy-4'-nitrobiphenyl
2143-90-0

4-methoxy-4'-nitrobiphenyl

Conditions
ConditionsYield
With sodium carbonate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;100%
With palladium diacetate; 4-Ph2P-C6H4-2-N-glucosamine; sodium carbonate In tetrahydrofuran; ethanol; water at 60℃; for 18h;99%
With polyhydroxylated phosphine; sodium carbonate; palladium diacetate In ethanol; water; toluene at 60℃; for 18h;99%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

4-methoxy-4'-nitrobiphenyl
2143-90-0

4-methoxy-4'-nitrobiphenyl

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 36h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With C12H10N3OPol; tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 100℃; for 15h; Suzuki-Miyaura reaction;99%
With sodium tetrachloropalladate(II); 5-[3-(4-carboxy-2,6-dimethylphenyl)-2-thioxoimidazolidin-1-yl]benzene-1,2,3-tricarboxylic acid; tetrabutylammomium bromide; potassium hydroxide In water at 100℃; for 10h; Temperature; Suzuki-Miyaura Coupling; Sealed tube;99%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

9,15-bis(trifluoromethylsulfonyloxy)<212,13><5.2>metacyclophane
135019-26-0

9,15-bis(trifluoromethylsulfonyloxy)<212,13><5.2>metacyclophane

C35H36O2

C35H36O2

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110 - 120℃; for 24h; Suzuki coupling reaction;100%
cyclopent-2-enone
930-30-3

cyclopent-2-enone

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

(R)-3-(4-methoxyphenyl)cyclopentan-1-one
155325-51-2

(R)-3-(4-methoxyphenyl)cyclopentan-1-one

Conditions
ConditionsYield
With potassium hydroxide; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; bis(ethylene)rhodium(I) chloride dimer In 1,4-dioxane; water at 50℃; for 1h;100%
With chlorobis(ethylene)rhodium(I) dimer; C22H20N2O4; potassium hydroxide In ethanol at 30℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;98%
With chlorobis(ethylene)rhodium(I) dimer; (R)-6,6'-dimethoxy-P2,P2,P2',P2'-tetrakis-[4-(trifluoromethyl)phenyl]-biphenyl-2,2'-bisphosphine; potassium hydroxide In water; toluene at 20℃; for 6.5h; Inert atmosphere; optical yield given as %ee; stereoselective reaction;96%
3-Bromothianaphthene
7342-82-7

3-Bromothianaphthene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

3-(4-methoxy-phenyl)-benzo[b]thiophene
24257-23-6

3-(4-methoxy-phenyl)-benzo[b]thiophene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 6h; Reflux; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 6h; Inert atmosphere; Reflux;100%
With di-1-adamantyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water; acetonitrile at 50℃; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;76%
With di-1-adamantyl(4-sulfonatobenzyl)phosphonium; palladium diacetate; sodium carbonate In water; acetonitrile at 50℃; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Glovebox;76%
tetrakis(triphenylphosphine) palladium(0) Suzuki-Miyaura reaction;52%
diphenyl diselenide
1666-13-3

diphenyl diselenide

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

p-methoxyphenyl phenyl selenide
80448-01-7

p-methoxyphenyl phenyl selenide

Conditions
ConditionsYield
With Cu NPs/Ac In dimethyl sulfoxide at 20 - 100℃; for 3h; Sealed tube; Sonication;100%
With indium tribromide In dimethyl sulfoxide at 130℃; for 20h;98%
With Oxone In ethanol at 60℃; for 2h; Solvent; Temperature; Schlenk technique;98%

5720-07-0Relevant articles and documents

Functionalised 2,2′-bipyridine ligands for the preparation of metallostars; X-ray structures of free ligands and preparation of copper(I) and silver(I) complexes

Constable, Edwin C.,Housecroft, Catherine E.,Neuburger, Markus,Poleschak, Ingo,Zehnder, Margareta

, p. 93 - 108 (2003)

2,2-Bipyridine ligands bearing functionalised aryl substituents have been prepared with the aim of subsequent functionalisation and the preparation of multinuclear metallostars. The key intermediates are compounds containing 4-methoxyphenyl substituents w

Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems

Miyamura, Hiroyuki,Yasukawa, Tomohiro,Zhu, Zhiyuan,Kobayashi, Shū

supporting information, p. 353 - 359 (2019/12/15)

Asymmetric 1,4-addition reactions with β,γ-unsaturated α-ketoesters are valuable because the resulting chiral ketoester compounds can be converted into various useful species that are often used as chiral building blocks in drug and natural product synthesis. However, β,γ-unsaturated α-ketoesters have two reactive points in terms of nucleophilic additions, which will lead to the 1,4-adduct, the 1,2-adduct and to the combined 1,4- and 1,2-adduct. Therefore, controlling this chemoselectivity is an important factor for the development of these transformations. Here, we developed an asymmetric 1,4-addition of aryl boronic acids to β,γ-unsaturated α-ketoesters by using heterogeneous chiral rhodium nanoparticle systems with a chiral diene ligand bearing a secondary amide moiety. The newly developed polydimethylsilane-immobilized rhodium nanoparticle catalysts showed high activity, high chemoselectivity, and excellent enantioselectivity, and this is the first heterogeneous catalytic system for this asymmetric reaction. Metal nanoparticle catalysts were recovered and reused without loss of activity or leaching of metal. (Figure presented.).

Pd- And Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B2(OH)4

Munteanu, Charissa,Spiller, Taylor E.,Qiu, Jun,Delmonte, Albert J.,Wisniewski, Steven R.,Simmons, Eric M.,Frantz, Doug E.

, p. 10334 - 10349 (2020/09/18)

Despite recent advancements in metal-catalyzed borylations of aryl (pseudo)halides, there is a continuing need to develop robust methods to access both early-stage and late-stage organoboron intermediates amendable for further functionalization. In particular, the development of general catalytic systems that operate under mild reaction conditions across a broad range of electrophilic partners remains elusive. Herein, we report the development and application of three catalytic systems (two Pd-based and one Ni-based) for the direct borylation of aryl (pseudo)halides using tetrahydroxydiboron (B2(OH)4). For the Pd-based catalyst systems, we have identified general reaction conditions that allow for the sequestration of halide ions through simple precipitation that results in catalyst loadings as low as 0.01 mol % (100 ppm) and reaction temperatures as low as room temperature. We also describe a complementary Ni-based catalyst system that employs simple unligated Ni(II) salts as an inexpensive alternative to the Pd-based systems for the borylation of aryl (pseudo)halides. Extrapolation of all three systems to a one-pot tandem borylation/Suzuki-Miyaura cross-coupling is also demonstrated on advanced intermediates and drug substances.

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