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247940-06-3

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247940-06-3 Usage

Reaction

Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates. Ligand employed in Suzuki coupling reactions involving aryl chlorides, bromides and triflates. Useful ligand for the Pd-catalyzed oxidation of alcohols in the presence of chlorobenzenes. Useful ligand for the Pd-catalyzed amination with ammonia equivalents. Ligand for the gold(I)-catalyzed intramolecular [4+2] cycloadditions involving 1,3-enynes and arylalkynes with alkenes. Ligand used in the palladium-catalyzed borylation of aryl bromdies. Ligand used in the palladium-catalyzed siliylation of aryl chlorides.

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 247940-06-3 differently. You can refer to the following data:
1. Ligand employed in an extremely general method for the Pd-catalyzed synthesis of aromaticamines using aryl chlorides, bromides and triflates.
2. suzuki reaction
3. 2-(Dicyclohexylphosphino)biphenyl is used as a catalyst for Suzuki coupling reactions.

General Description

CyJohnPhos [(2-Biphenyl)dicyclohexylphosphine] is an air-stable, bulky and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 247940-06-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,7,9,4 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 247940-06:
(8*2)+(7*4)+(6*7)+(5*9)+(4*4)+(3*0)+(2*0)+(1*6)=153
153 % 10 = 3
So 247940-06-3 is a valid CAS Registry Number.
InChI:InChI=1/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2

247940-06-3 Well-known Company Product Price

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  • TCI America

  • (D3388)  2-(Dicyclohexylphosphino)biphenyl  >98.0%(GC)

  • 247940-06-3

  • 1g

  • 620.00CNY

  • Detail
  • TCI America

  • (D3388)  2-(Dicyclohexylphosphino)biphenyl  >98.0%(GC)

  • 247940-06-3

  • 5g

  • 2,310.00CNY

  • Detail
  • Aldrich

  • (638099)  CyJohnPhos  97%

  • 247940-06-3

  • 638099-1G

  • 725.40CNY

  • Detail
  • Aldrich

  • (638099)  CyJohnPhos  97%

  • 247940-06-3

  • 638099-5G

  • 2,694.51CNY

  • Detail
  • Aldrich

  • (638099)  CyJohnPhos  97%

  • 247940-06-3

  • 638099-25G

  • 10,928.97CNY

  • Detail

247940-06-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name dicyclohexyl-(2-phenylphenyl)phosphane

1.2 Other means of identification

Product number -
Other names [1,1'-Biphenyl]-2-yldicyclohexylphosphine

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:247940-06-3 SDS

247940-06-3Synthetic route

methanol
67-56-1

methanol

(2-biphenyl)dicyclohexylphosphane-borane(1:1)
1186392-99-3

(2-biphenyl)dicyclohexylphosphane-borane(1:1)

A

Trimethyl borate
121-43-7

Trimethyl borate

B

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;A n/a
B 97%
([1,1’-biphenyl]-2-yl)dicyclohexylphosphine oxide

([1,1’-biphenyl]-2-yl)dicyclohexylphosphine oxide

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
With 1,3-diphenyl-disiloxane In toluene at 110℃; Sealed tube; chemoselective reaction;93%
With diisobutylaluminium hydride In various solvent(s) at 125℃; for 4h;
Multi-step reaction with 2 steps
1: oxalyl dichloride / dichloromethane / 1 h / 20 °C / Schlenk technique; Inert atmosphere; Sealed tube
2: hexachlorodisilane / dichloromethane-d2 / 0.08 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox
View Scheme
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

dicyclohexylphosphane
829-84-5

dicyclohexylphosphane

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); potassium hydroxide In water at 100℃; Inert atmosphere;81%
iodobenzene
591-50-4

iodobenzene

dicyclohexyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]phosphine borane
1417911-72-8

dicyclohexyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]phosphine borane

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
Stage #1: iodobenzene; dicyclohexyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]phosphine borane With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium hydroxide In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; Inert atmosphere;
81%
biphenyl-2-yl trifluoromethanesulfonate
17763-65-4

biphenyl-2-yl trifluoromethanesulfonate

dicyclohexylphosphane
829-84-5

dicyclohexylphosphane

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In N,N-dimethyl-formamide at 100℃; for 18.67h; Product distribution / selectivity;77%
With 1,4-diaza-bicyclo[2.2.2]octane; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In N,N-dimethyl-formamide at 100℃; for 18.67h; Product distribution / selectivity;8 %Chromat.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel dichloride In water; N,N-dimethyl-formamide at 100℃; for 18.67h; Product distribution / selectivity;90 %Chromat.
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

chlorodicyclohexylphosphane
16523-54-9

chlorodicyclohexylphosphane

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
Stage #1: 2-Bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Metallation;
Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -78 - 0℃; for 14h; Condensation;
71%
Stage #1: 2-Bromobiphenyl With n-butyllithium In diethyl ether; hexane at 0℃; for 2h;
Stage #2: chlorodicyclohexylphosphane In diethyl ether; hexane at 20℃; for 1h;
ethanol
64-17-5

ethanol

(2-biphenyl)dicyclohexylphosphane-borane(1:1)
1186392-99-3

(2-biphenyl)dicyclohexylphosphane-borane(1:1)

A

triethyl borate
150-46-9

triethyl borate

B

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 52%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,2-dimethoxyethane / 5 h / 80 °C / Inert atmosphere
2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C
2.2: 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,2-dimethoxyethane; water / 5 h / 80 °C / Inert atmosphere
2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C
2.2: 1 h / 20 °C
View Scheme
phenylboronic acid
98-80-6

phenylboronic acid

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,2-dimethoxyethane / 5 h / 80 °C / Inert atmosphere
2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C
2.2: 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,2-dimethoxyethane; water / 5 h / 80 °C / Inert atmosphere
2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C
2.2: 1 h / 20 °C
View Scheme
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

Cy2P-Hal

Cy2P-Hal

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
Stage #1: 2-Bromobiphenyl With n-butyllithium In diethyl ether; hexane at 0℃; for 2h;
Stage #2: Cy2P-Hal In diethyl ether; hexane at 20℃; for 1h;
1-chloro-3-methyl-1-phenyl-2-phospholenium chloride

1-chloro-3-methyl-1-phenyl-2-phospholenium chloride

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
With hexachlorodisilane In dichloromethane-d2 at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Glovebox;333 mg
CyJohnPhos
247940-06-3

CyJohnPhos

(2-biphenyl)dicyclohexylphosphane-borane(1:1)
1186392-99-3

(2-biphenyl)dicyclohexylphosphane-borane(1:1)

Conditions
ConditionsYield
Stage #1: CyJohnPhos With dimethylsulfide borane complex In dichloromethane at 20℃; Inert atmosphere;
Stage #2: With ammonium chloride In dichloromethane; water
100%
(tetrahydrothiophene)gold(I) chloride
39929-21-0

(tetrahydrothiophene)gold(I) chloride

CyJohnPhos
247940-06-3

CyJohnPhos

chloro([1,1'-biphenyl]-2-yldicyclohexylphosphine)gold(I)
854045-92-4

chloro([1,1'-biphenyl]-2-yldicyclohexylphosphine)gold(I)

Conditions
ConditionsYield
In dichloromethane for 1.75h;100%
In dichloromethane at 20℃;46%
In dichloromethane at 20℃; for 1h; Darkness;
CyJohnPhos
247940-06-3

CyJohnPhos

([1,1’-biphenyl]-2-yl)dicyclohexylphosphine oxide

([1,1’-biphenyl]-2-yl)dicyclohexylphosphine oxide

Conditions
ConditionsYield
With dihydrogen peroxide In dichloromethane at 20℃; for 1h;99%
With dihydrogen peroxide In water; acetone for 3h;93%
With oxygen In toluene at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;
hydrogen tetrachloroaurate(III) tetrahydrate

hydrogen tetrachloroaurate(III) tetrahydrate

CyJohnPhos
247940-06-3

CyJohnPhos

chloro([1,1'-biphenyl]-2-yldicyclohexylphosphine)gold(I)
854045-92-4

chloro([1,1'-biphenyl]-2-yldicyclohexylphosphine)gold(I)

Conditions
ConditionsYield
Stage #1: hydrogen tetrachloroaurate(III) tetrahydrate With propyl sulfide In ethanol at 40℃; for 0.166667h;
Stage #2: CyJohnPhos In ethanol at 40℃; for 1h;
97%
4-bromo-1-methyl-1H-indole
590417-55-3

4-bromo-1-methyl-1H-indole

CyJohnPhos
247940-06-3

CyJohnPhos

4,4'-(2'-(dicyclohexylphosphino)biphenyl-2,6-diyl)bis(1-methyl-1H-indole)

4,4'-(2'-(dicyclohexylphosphino)biphenyl-2,6-diyl)bis(1-methyl-1H-indole)

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;96%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;96%
copper(II) tetrafluroborate hexahydrate

copper(II) tetrafluroborate hexahydrate

CyJohnPhos
247940-06-3

CyJohnPhos

BF4(1-)*C24H30P(1+)

BF4(1-)*C24H30P(1+)

Conditions
ConditionsYield
In acetonitrile at 100℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;96%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

CyJohnPhos
247940-06-3

CyJohnPhos

2-(dicyclohexylphosphino)-2’-(3-methoxy-3-oxopropyl)biphenyl

2-(dicyclohexylphosphino)-2’-(3-methoxy-3-oxopropyl)biphenyl

Conditions
ConditionsYield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;96%
copper(I) triflate benzene complex

copper(I) triflate benzene complex

CyJohnPhos
247940-06-3

CyJohnPhos

[(CyJohnPhos)Cu][OTf]

[(CyJohnPhos)Cu][OTf]

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Inert atmosphere;95%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

CyJohnPhos
247940-06-3

CyJohnPhos

2-dicyclohexylphosphino-2',6'-bis(4-cyanophenyl)biphenyl

2-dicyclohexylphosphino-2',6'-bis(4-cyanophenyl)biphenyl

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;95%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;95%
acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

CyJohnPhos
247940-06-3

CyJohnPhos

2-(dicyclohexylphosphino)-2’-(3-n-butoxy-3-oxopropyl)biphenyl

2-(dicyclohexylphosphino)-2’-(3-n-butoxy-3-oxopropyl)biphenyl

Conditions
ConditionsYield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;95%
bis(1,5-cyclooctadiene)diiridium(I) dichloride
12112-67-3

bis(1,5-cyclooctadiene)diiridium(I) dichloride

CyJohnPhos
247940-06-3

CyJohnPhos

[IrCl(COD)(2-(dicyclohexylphosphino)biphenyl)]
1268489-02-6

[IrCl(COD)(2-(dicyclohexylphosphino)biphenyl)]

Conditions
ConditionsYield
In toluene under Ar atm. using Schlenk techniques; mixt. of Ir complex and ligand in dry toluene was stirred at room temp. for 3 h; solvent evapd.; acetone added; suspn. filtered; washed (acetone); elem. anal.;94%
p-trifluoromethylphenyl bromide
402-43-7

p-trifluoromethylphenyl bromide

CyJohnPhos
247940-06-3

CyJohnPhos

2-dicyclohexylphosphino-2',6'-bis(4-trifluoromethylphenyl)biphenyl

2-dicyclohexylphosphino-2',6'-bis(4-trifluoromethylphenyl)biphenyl

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 150℃; for 36h; Temperature; Concentration; Schlenk technique; Inert atmosphere;94%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;87%
3,6-bis(trifluoromethyl)bromobenzene
328-70-1

3,6-bis(trifluoromethyl)bromobenzene

CyJohnPhos
247940-06-3

CyJohnPhos

2-dicyclohexylphosphino-2',6'-bis(3,5-ditrifluoromethylphenyl)biphenyl

2-dicyclohexylphosphino-2',6'-bis(3,5-ditrifluoromethylphenyl)biphenyl

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 150℃; for 36h; Temperature; Concentration; Schlenk technique; Inert atmosphere;94%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;89%
bromobenzene
108-86-1

bromobenzene

CyJohnPhos
247940-06-3

CyJohnPhos

2',6'-diphenylbiphenyl-2-yldicyclohexylphosphine

2',6'-diphenylbiphenyl-2-yldicyclohexylphosphine

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;94%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Concentration; Temperature; Schlenk technique; Inert atmosphere;94%
C60H24Cl3F18N3Pd3

C60H24Cl3F18N3Pd3

CyJohnPhos
247940-06-3

CyJohnPhos

C44H39ClF6NPPd

C44H39ClF6NPPd

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;94%
2,3,4,5-tetrakis(pentafluorophenyl)cyclopenta-2,4-dien-1-one
15070-92-5

2,3,4,5-tetrakis(pentafluorophenyl)cyclopenta-2,4-dien-1-one

CyJohnPhos
247940-06-3

CyJohnPhos

C53H31F20OP

C53H31F20OP

Conditions
ConditionsYield
In toluene at 20℃; Inert atmosphere;93%
para-bromotoluene
106-38-7

para-bromotoluene

CyJohnPhos
247940-06-3

CyJohnPhos

2-dicyclohexylphosphino-2',6'-bis(4-methylphenyl)biphenyl

2-dicyclohexylphosphino-2',6'-bis(4-methylphenyl)biphenyl

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;93%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;93%
(-)-menthyl acrylate
4835-96-5

(-)-menthyl acrylate

CyJohnPhos
247940-06-3

CyJohnPhos

2-(dicyclohexylphosphino)-2’-(3-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-3-oxopropyl)biphenyl

2-(dicyclohexylphosphino)-2’-(3-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-3-oxopropyl)biphenyl

Conditions
ConditionsYield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;93%
trifluoro-methanesulfonic acid 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl ester
779344-65-9

trifluoro-methanesulfonic acid 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl ester

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

CyJohnPhos
247940-06-3

CyJohnPhos

6-(4-Methoxy-phenyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile
779344-69-3

6-(4-Methoxy-phenyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate In toluene92%
bis(1,5-cyclooctadiene)diiridium(I) dichloride
12112-67-3

bis(1,5-cyclooctadiene)diiridium(I) dichloride

CyJohnPhos
247940-06-3

CyJohnPhos

(COD)Ir(2-(dicyclohexylphosphino)biphenyl)Cl
1268489-02-6

(COD)Ir(2-(dicyclohexylphosphino)biphenyl)Cl

Conditions
ConditionsYield
In dichloromethane at 20℃;92%
chlorobenzene
108-90-7

chlorobenzene

CyJohnPhos
247940-06-3

CyJohnPhos

2',6'-diphenylbiphenyl-2-yldicyclohexylphosphine

2',6'-diphenylbiphenyl-2-yldicyclohexylphosphine

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 150℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique;92%
1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

CyJohnPhos
247940-06-3

CyJohnPhos

2-dicyclohexylphosphino-2',6'-bis(4-fluorophenyl)biphenyl

2-dicyclohexylphosphino-2',6'-bis(4-fluorophenyl)biphenyl

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;92%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;92%
4-Iodobenzotrifluoride
455-13-0

4-Iodobenzotrifluoride

CyJohnPhos
247940-06-3

CyJohnPhos

dicyclohexyl(4''-(trifluoromethyl)-[1,1':2',1''-terphenyl]-2-yl)phosphane

dicyclohexyl(4''-(trifluoromethyl)-[1,1':2',1''-terphenyl]-2-yl)phosphane

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; iodine; potassium acetate; 1-amino-1-cyclopentanecarboxylic acid; acetylacetone In cyclohexane at 160℃; for 16h; Inert atmosphere; Sealed tube; Schlenk technique;92%
4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

CyJohnPhos
247940-06-3

CyJohnPhos

2-dicyclohexylphosphino-2',6'-bis(4-dimethylaminophenyl)biphenyl

2-dicyclohexylphosphino-2',6'-bis(4-dimethylaminophenyl)biphenyl

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;91%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;91%
ethyl acrylate
140-88-5

ethyl acrylate

CyJohnPhos
247940-06-3

CyJohnPhos

2-(dicyclohexylphosphino)-2’-(3-ethoxy-3-oxopropyl)biphenyl

2-(dicyclohexylphosphino)-2’-(3-ethoxy-3-oxopropyl)biphenyl

Conditions
ConditionsYield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;91%
methyl 3-iodo-benzoate
618-91-7

methyl 3-iodo-benzoate

CyJohnPhos
247940-06-3

CyJohnPhos

methyl 2''-(dicyclohexylphosphanyl)-[1,1':2',1''-terphenyl]-3-carboxylate

methyl 2''-(dicyclohexylphosphanyl)-[1,1':2',1''-terphenyl]-3-carboxylate

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; iodine; potassium acetate; 1-amino-1-cyclopentanecarboxylic acid; acetylacetone In cyclohexane at 160℃; for 16h; Inert atmosphere; Sealed tube; Schlenk technique;91%
bis[(1,2,3-η)-2-butenyl]di(μ-chloro)palladium(II)

bis[(1,2,3-η)-2-butenyl]di(μ-chloro)palladium(II)

CyJohnPhos
247940-06-3

CyJohnPhos

[(η3-syn-crotyl)PdCl(dicyclohexylphosphino-2-biphenyl)]
692782-19-7

[(η3-syn-crotyl)PdCl(dicyclohexylphosphino-2-biphenyl)]

Conditions
ConditionsYield
In tetrahydrofuran (N2); THF was added via syringe to mixt. of Pd compd. and P ligand in Schlenk flask; soln. was stirred at room temp. for 1 h; evapd. (vac.); washed (pentane); elem. anal.;90%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

CyJohnPhos
247940-06-3

CyJohnPhos

2-dicyclohexylphosphino-2',6'-bis(3,5-dimethylphenyl)biphenyl

2-dicyclohexylphosphino-2',6'-bis(3,5-dimethylphenyl)biphenyl

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;90%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;90%

247940-06-3Relevant articles and documents

Palladium-Catalyzed C-P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines

Chen, Xingyu,Wu, Hongyu,Yu, Rongrong,Zhu, Hong,Wang, Zhiqian

, p. 8987 - 8996 (2021/06/30)

Palladium-catalyzed C-P bond formation reaction of ArBr/ArOTf using acylphosphines as differential phosphination reagents is reported. The acylphosphines show practicable reactivity with ArBr and ArOTf as the phosphination reagents, though they are inert to the air and moisture. The reaction affords trivalent phosphines directly in good yields with a broad substrate scope and functional group tolerance. This reaction discloses the acylphosphines' capability as new phosphorus sources for the direct synthesis of trivalent phosphines.

Rhodium-Catalyzed PIII-Directed ortho-C?H Borylation of Arylphosphines

Wen, Jian,Wang, Dingyi,Qian, Jiasheng,Wang, Di,Zhu, Chendan,Zhao, Yue,Shi, Zhuangzhi

supporting information, p. 2078 - 2082 (2019/02/01)

Transition-metal-mediated metalation of an aromatic C?H bond that is adjacent to a tertiary phosphine group in arylphosphines via a four-membered chelate ring was first discovered in 1968. Herein, we overcome a long-standing problem with the ortho-C?H activation of arylphosphines in a catalytic fashion. In particular, we developed a rhodium-catalyzed ortho-selective C?H borylation of various commercially available arylphosphines with B2pin2 through PIII-chelation-assisted C?H activation. This discovery is suggestive of a generic platform that could enable the late-stage modification of readily accessible arylphosphines.

Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane

Buonomo, Joseph A.,Eiden, Carter G.,Aldrich, Courtney C.

supporting information, p. 14434 - 14438 (2017/10/23)

Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously calculated silane reduction system. Inclusion of a catalytic Br?nsted acid further reduced the activation barrier and led to the first silane-mediated reduction of acyclic phosphine oxides at room temperature.

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