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10540-31-5 Usage

General Description

4-(4-Fluorophenyl)benzonitrile is a chemical compound with the molecular formula C13H8FN. It is a white solid that is insoluble in water but soluble in organic solvents. 4-(4-Fluorophenyl)benzonitrile is used in the synthesis of pharmaceuticals and agrochemicals, as well as in research applications. It is a benzonitrile derivative, and its fluorophenyl group makes it useful for the development of fluorescent dyes and materials. 4-(4-Fluorophenyl)benzonitrile is also used as a building block in organic synthesis, particularly in the preparation of biologically active compounds. Due to its specific structure and properties, it has potential applications in various industries, including pharmaceuticals, materials, and research.

Check Digit Verification of cas no

The CAS Registry Mumber 10540-31-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,5,4 and 0 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 10540-31:
(7*1)+(6*0)+(5*5)+(4*4)+(3*0)+(2*3)+(1*1)=55
55 % 10 = 5
So 10540-31-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H8FN/c14-13-7-5-12(6-8-13)11-3-1-10(9-15)2-4-11/h1-8H

10540-31-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(4-Fluorophenyl)benzonitrile

1.2 Other means of identification

Product number -
Other names 4-fluoro-4'-cyanobiphenyl

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:10540-31-5 SDS

10540-31-5Synthetic route

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.0833333h; Suzuki cross-coupling;99%
With potassium carbonate; polymer-supported Pd catalyst FC 1001 In ethanol at 110℃; for 0.166667h; Suzuki coupling; microwave irradiation;98%
With Ph2P(CH2CH2O)22CH3; triethylamine; palladium dichloride In water at 80℃; for 1h; Suzuki coupling; Inert atmosphere;98%
4-cyanophenyl trifluoromethanesulfonate
66107-32-2

4-cyanophenyl trifluoromethanesulfonate

potassim 4-fluorophenyltrifluoroborate

potassim 4-fluorophenyltrifluoroborate

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With palladium diacetate In ethanol at 95℃; for 0.25h; microwave irradiation;99%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
Stage #1: 4-Cyanochlorobenzene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran; toluene Kumada Cross-Coupling; Inert atmosphere; Sealed tube;
Stage #2: 4-flourophenylmagnesium bromide In tetrahydrofuran; toluene at 20℃; for 1.5h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube; chemoselective reaction;
98%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

potassim 4-fluorophenyltrifluoroborate

potassim 4-fluorophenyltrifluoroborate

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In methanol for 2h; Suzuki-Miyaura cross-coupling; Heating;96%
With potassium carbonate; palladium diacetate In methanol for 2h; Suzuki reaction; Heating;96%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With C23H20ClFeN3Pd; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 4h; Reagent/catalyst; Suzuki-Miyaura Coupling;95%
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

4-cyanophenol
767-00-0

4-cyanophenol

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
Stage #1: 4-cyanophenol With fluorosulfonyl fluoride; triethylamine In ethanol; water at 20℃; for 4h;
Stage #2: 4-fluoroboronic acid With palladium diacetate; triethylamine In ethanol; water at 20℃; for 6h;
95%
4-cyanophenyl sulfurofluoridate

4-cyanophenyl sulfurofluoridate

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With palladium diacetate; triethylamine In water at 20℃; for 2h; Suzuki-Miyaura Coupling;94%
2-(4-fluorophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

2-(4-fluorophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

4-cyanobenzene-1-sulfonyl fluoride
33719-37-8

4-cyanobenzene-1-sulfonyl fluoride

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; diisopropylamine In ethanol; water at 45℃; for 4h;94%
4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

tributyl(4-fluorophenyl)stannane
17151-47-2

tributyl(4-fluorophenyl)stannane

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; diamminedichloropalladium(II); sodium hydrogencarbonate In water at 110℃; for 3h; Stille Cross Coupling; Sealed tube;93%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
214360-58-4

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

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere;92.5%
(4-cyanophenyl)magnesium bromide
412044-48-5

(4-cyanophenyl)magnesium bromide

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)magnesium bromide; 4-flourophenylmagnesium bromide With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -10℃; Inert atmosphere;
Stage #2: With oxygen In tetrahydrofuran at 10 - 20℃;
91%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane
225916-39-2

2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With P(t-Bu)3 Palladacycle Gen. 3; potassium trimethylsilonate In tetrahydrofuran at 23℃; for 0.25h; Suzuki-Miyaura Coupling;91%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

2-(4-fluorophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

2-(4-fluorophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With palladium diacetate; diisopropylamine In water at 100℃; for 1h; Suzuki-Miyaura Coupling;88%
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

4-[(trifluoromethyl)sulfonyl] benzonitrile
312-21-0

4-[(trifluoromethyl)sulfonyl] benzonitrile

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With potassium phosphate; palladium(II) acetylacetonate; ruphos In 1,4-dioxane; dimethyl sulfoxide at 80℃; for 16h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;82%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

(4-fluorophenyl)zinc pivalate

(4-fluorophenyl)zinc pivalate

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride In tetrahydrofuran at 25℃; for 2h; Negishi Coupling Reaction;80%
4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

tris(4-fluorophenyl)bismuthane
437-29-6

tris(4-fluorophenyl)bismuthane

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With potassium acetate; palladium diacetate; N-cyclohexyl-cyclohexanamine In N,N-dimethyl-formamide at 35℃; for 2h; Inert atmosphere;78%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

4′-fluoro-[1,1'-biphenyl]-4-yl methanesulfonate

4′-fluoro-[1,1'-biphenyl]-4-yl methanesulfonate

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With dmap; nickel(II) bromide dimethoxyethane; 1,4-di(diphenylphosphino)-butane; zinc In acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere;77%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

triallyl(4-fluorophenyl)silane
725735-33-1

triallyl(4-fluorophenyl)silane

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
Stage #1: triallyl(4-fluorophenyl)silane With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 1h;
Stage #2: 4-Cyanochlorobenzene With XPhos; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; water at 80℃; for 11h;
73%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-fluorophenyhydrazine hydrochloride
823-85-8

4-fluorophenyhydrazine hydrochloride

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 8h;71%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

triallyl(4-fluorophenyl)silane
725735-33-1

triallyl(4-fluorophenyl)silane

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
Stage #1: triallyl(4-fluorophenyl)silane With tetrabutyl ammonium fluoride In water; dimethyl sulfoxide at 20℃; for 1h;
Stage #2: 4-bromobenzenecarbonitrile With tricyclohexylphosphine; palladium dichloride In water; dimethyl sulfoxide at 80℃; for 18h;
69%
N-(4-cyanophenyl)acetamide
35704-19-9

N-(4-cyanophenyl)acetamide

potassim 4-fluorophenyltrifluoroborate

potassim 4-fluorophenyltrifluoroborate

A

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

B

4,4'-difluorobiphenyl
398-23-2

4,4'-difluorobiphenyl

Conditions
ConditionsYield
Stage #1: N-(4-cyanophenyl)acetamide With boron trifluoride methanol complex In methanol at 65℃; Inert atmosphere;
Stage #2: With tert.-butylnitrite In methanol at 0℃; for 1h; Inert atmosphere;
Stage #3: potassim 4-fluorophenyltrifluoroborate With palladium diacetate In methanol at 20℃; for 12.25h; Suzuki Coupling; Inert atmosphere;
A 65%
B 10%
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

N-methyl-di-4-cyanobenzenesulfonamide

N-methyl-di-4-cyanobenzenesulfonamide

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 110℃; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;51%
C25H16BF3N(1-)*K(1+)

C25H16BF3N(1-)*K(1+)

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; oxygen In acetonitrile at 50℃; for 16h; Inert atmosphere; Irradiation;47%
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

1-(methylsulfonyl)-2-(4-cyanophenyl)diazene

1-(methylsulfonyl)-2-(4-cyanophenyl)diazene

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With [2,2]bipyridinyl; (triphenylphosphine)gold(I) chloride; sodium acetate In methanol; acetonitrile for 16h; Suzuki Coupling; Inert atmosphere; Irradiation;37%
4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

Conditions
ConditionsYield
With sodium carbonate In methanol at 150℃; for 1h; Suzuki-Miyaura Coupling; Microwave irradiation;8%
4-fluorobenzenediazonium tetrafluoroborate
459-45-0

4-fluorobenzenediazonium tetrafluoroborate

benzonitrile
100-47-0

benzonitrile

A

4'-fluoro-[1,1'-biphenyl]-3-carbonitrile
10540-33-7

4'-fluoro-[1,1'-biphenyl]-3-carbonitrile

B

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

C

4'-fluoro-[1,1'-biphenyl]-2-carbonitrile
89346-55-4

4'-fluoro-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
With potassium acetate; 18-crown-6 ether for 1.5h; Ambient temperature; Yield given. Yields of byproduct given;
methanol
67-56-1

methanol

4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

4'-fluoro-N-methyl-[1,1'-biphenyl]-4-carboxamide

4'-fluoro-N-methyl-[1,1'-biphenyl]-4-carboxamide

Conditions
ConditionsYield
With tris(2-diphenylphosphinoethyl)phosphine; potassium tert-butylate; water; caesium carbonate; cobalt(II) bromide In m-xylene at 140℃; for 24h; Green chemistry;97%
4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

4-fluoro-biphenyl
324-74-3

4-fluoro-biphenyl

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); hydrogen; trimethylaluminum; tricyclohexylphosphine In toluene at 130℃; under 750.075 Torr; for 24h; Schlenk technique;82%
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; ethanol; potassium hexamethylsilazane In toluene at 150℃; for 8h; Inert atmosphere; Molecular sieve;58%
4-cyano-4'-fluorobiphenyl
10540-31-5

4-cyano-4'-fluorobiphenyl

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

1-(4'-fluoro-[1,1'-biphenyl]-4-yl)cyclopropan-1-amine

1-(4'-fluoro-[1,1'-biphenyl]-4-yl)cyclopropan-1-amine

Conditions
ConditionsYield
Stage #1: 4-cyano-4'-fluorobiphenyl; ethylmagnesium bromide With titanium(IV) isopropylate In diethyl ether at 0 - 20℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In diethyl ether at 20℃; for 2h;
39.1%

10540-31-5Relevant articles and documents

Cost-effective bio-derived mesoporous carbon nanoparticles-supported palladium catalyst for nitroarene reduction and Suzuki–Miyaura coupling by microwave approach

Supriya,Ananthnag, Guddekoppa S.,Shetti, Vijayendra S.,Nagaraja,Hegde, Gurumurthy

, (2020)

A new heterogeneous catalyst was synthesized by immobilizing Pd on areca nut kernel-derived carbon nanospheres (CNSs). The CNSs, without any further activation processes, accommodated 3% of Pd on their surface. The new Pd/CNS material was used for the reduction of nitroarenes and Suzuki–Miyaura coupling of bromoarenes with aryl boronic acids. The reactions were conducted under microwave irradiation at 160 °C using 12 mol% of Pd/CNS (0.36% actual Pd content). The reduction of nitroarenes into their respective amino compounds was achieved in 10–20 min (conversion up to 100%); by contrast, the Suzuki–Miyaura reactions yielded up to 98% at 150 °C with 10 mol% of Pd/CNS catalyst. The products were identified using gas chromatography and nuclear magnetic resonance spectroscopy. The catalyst was isolated from reaction mixture and reused without any significant loss in the activity. Thus, the present work introduces one-pot-derived porous CNSs as efficient catalytic support to Pd, establishing an alternative to existing Pd/C in terms of cost and efficiency.

Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates

Liang, Qiaobin,Xing, Ping,Huang, Zuogang,Dong, Jiajia,Sharpless, K. Barry,Li, Xiaoxian,Jiang, Biao

, p. 1942 - 1945 (2015)

Aryl fluorosulfates were prepared by a simple method and employed as coupling partners in the Suzuki-Miyaura reaction. The cross-coupling reactions were performed in water under air at room temperature without ligands or additives such as surfactants or phase-transfer reagents and proceeded smoothly to give excellent yields. Aryl fluorosulfates could also be used as alternatives to halides or triflates in other coupling reactions.

Suzuki–Miyaura Coupling of (Hetero)Aryl Sulfones: Complementary Reactivity Enables Iterative Polyaryl Synthesis

Chatelain, Paul,Sau, Abhijit,Rowley, Christopher N.,Moran, Joseph

, p. 14959 - 14963 (2019)

Ideal organic syntheses involve the rapid construction of C?C bonds, with minimal use of functional group interconversions. The Suzuki–Miyaura cross-coupling (SMC) is a powerful way to form biaryl linkages, but the relatively similar reactivity of electrophilic partners makes iterative syntheses involving more than two sequential coupling events difficult to achieve without additional manipulations. Here we introduce (hetero)aryl sulfones as electrophilic coupling partners for the SMC reaction, which display an intermediate reactivity between those of typical aryl (pseudo)halides and nitroarenes. The new complementary reactivity allows for rapid sequential cross-coupling of arenes bearing chloride, sulfone and nitro leaving groups, affording non-symmetric ter- and quateraryls in only 2 or 3 steps, respectively. The SMC reactivity of (hetero)aryl sulfones is demonstrated in over 30 examples. Mechanistic experiments and DFT calculations are consistent with oxidative addition into the sulfone C?S bond as the turnover-limiting step. The further development of electrophilic cross-coupling partners with complementary reactivity may open new possibilities for divergent iterative synthesis starting from small pools of polyfunctionalized arenes.

Pd-nanoparticles catalyzed denitrogenative coupling of aryl halides with arylhydrazines: Greener approach for biaryls synthesis under ligand-free condition

Hegde, Rajeev V.,Ghosh, Arnab,Patil, Siddappa A.,Dateer, Ramesh B.

, (2019)

The greener approach for the synthesis of biaryl using palladium nanoparticle (Pd–NPs) catalyzed denitrogenative coupling between aryl hydrazine and aryl halides under ligand-free condition has been described. The phytochemicals of the black pepper extract plays a dual role in reduction of PdII to Pd0 and acts as stabilizing agent for Pd–NPs. The electronically diver's arylhydrazines and commercially available aryl halides are used for the synthesis of symmetrical and unsymmetrical biaryls in good to excellent yield. The mechanism is well supported by control experiment and the recyclability, turnover number and turnover frequency of biogenically synthesized Pd–NPs is studied.

Microwave enhanced ligand- and base-free cross-coupling of potassium aryltrifluoroborates salts with aryl triflates

Kabalka, George W.,Zhou, Li-Li,Naravane, Abhijit

, p. 6887 - 6889 (2006)

A microwave enhanced ligand- and base-free protocol for the cross-coupling of potassium aryltrifluoroborate salts with triflates is reported.

A simple and mild Suzuki reaction protocol using triethylamine as base and solvent

Li, Xinmin,Zhang, Hang,Hu, Qinghong,Jiang, Bo,Zeli, Yuan

, p. 3123 - 3132 (2018)

A simple and mild protocol for the palladium-catalyzed Suzuki reaction of aryl bromides and arylboronic acids is developed. The cross-coupling reactions can be performed at room temperature using 5.0 equiv. of Et3N as solvent and base without any ligands, and affording biaryl products in good yields. In addition, the chemoselecitive Suzuki reaction of bromo-N-methyliminodiacetic acid (MIDA) boronates with arylboronic acids can be achieved in this system, and various unsymmetrical terphenyls have been prepared in moderate yields by one-pot double Suzuki reactions.

Palladium nanoparticle supported on nitrogen-doped porous carbon: Investigation of structural properties and catalytic activity on Suzuki–Miyaura reactions

Bu?day, Nesrin,Alt?n, Serdar,Ya?ar, Sedat

, (2021)

Novel palladium-doped nanoporous carbon composite material obtained via thermolysis of amorphous zeolitic imidazolate framework (aZIF) was synthesized and used as an efficient catalyst on Suzuki–Miyaura cross-coupling reactions of aryl bromides. With this developed catalytic system, the Suzuki–Miyaura cross-coupling reaction was accomplished in aqueous solutions, and biaryls were obtained in good to excellent yields in a short reaction time. The APC-750@Pd catalyst was characterized by Fourier Transform Infrared spectroscopy (FTIR), X-ray Diffraction (XRD), Scanning Electron Eicroscopy (SEM), X-ray Photoelectron Spectroscopy (XPS), Transmission Electron Microscopy (TEM), Thermal Gravimetric Analysis (TGA), Differential Thermal Analysis (DTA), Inductively Coupled Plasma Mass Spectrometry (ICP-MS) and Brunauer–Emmett–Teller (BET) analysis tecniques. N-doped porous carbon material (NPC-1000) was synthesized by thermolysis from aZIF. Activated porous carbon material (APC-750) was fabricated via fused at 750°C with KOH from NPC-1000. The APC-750@Pd was obtained as a result of the interaction of APC-750 and PdCl2 in deionized water. The cross-coupling reaction of different aryl bromides with phenylboronic acid was investigated to show the potential of the APC-750@Pd in the Suzuki–Miyaura cross-coupling reactions. The APC-750@Pd catalyst could be recycled at least five times with a 15% loss of catalytic efficiency in this catalytic system.

Palladium-catalyzed Suzuki-Miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates

Zhang, Liang,Meng, Tianhao,Wu, Jie

, p. 9346 - 9349 (2007)

(Chemical Equation Presented) Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl tosylates with potassium aryl trifluoroborate in the presence of bulky and electron-rich phosphine ligand is described. In addition, a useful chemoselective coupling of an aryl chloride in the presence of a tosyloxy group was demonstrated.

Highly Active Bimetallic Nickel-Palladium Alloy Nanoparticle Catalyzed Suzuki-Miyaura Reactions

Rai, Rohit Kumar,Gupta, Kavita,Behrens, Silke,Li, Jun,Xu, Qiang,Singh, Sanjay Kumar

, p. 1806 - 1812 (2015)

A bimetallic Ni-Pd alloy nanoparticle catalyst with a low palladium content (Ni0.90Pd0.10 nanocatalyst) was prepared and its catalytic performance in Suzuki-Miyaura reactions was evaluated along with that of other Ni-Pd nanocatalysts (with varying Ni/Pd molar ratios in the range of ≈0.25-0.75) and the corresponding monometallic, Ni and Pd, analogues. Notably, the bimetallic Ni0.90Pd0.10 alloy nanocatalyst performed exceptionally well for the synthesis of biaryls by employing a wide range of substituted aryl halides and arylboronic acids having electron-donating and electron-withdrawing groups, and they exhibited high recyclability in water/ethanol solution at moderate reaction temperatures. Catalyst poisoning tests and leaching experiments inferred the heterogeneous nature of the Ni0.90Pd0.10 nanocatalysts. The significant synergistic interactions between Ni and Pd account for the observed high catalytic efficacy of the Ni0.90Pd0.10 nanocatalyst. Up, up, and alloy! Highly active bimetallic Ni-Pd alloy nanocatalysts with high Ni/Pd molar ratios facilitate the Suzuki-Miyaura reactions of a wide range of aryl iodides/bromides and arylboronic acids to biaryls in high yields at moderate temperatures in water/ethanol solution. High synergistic interaction between Ni and Pd accounts for the observed high activity and recyclability of the bimetallic Ni-Pd nanocatalysts. FG=functional group.

Photocatalyzed Transition-Metal-Free Oxidative Cross-Coupling Reactions of Tetraorganoborates**

Music, Arif,Baumann, Andreas N.,Boser, Florian,Müller, Nicolas,Matz, Florian,Jagau, Thomas C.,Didier, Dorian

supporting information, p. 4322 - 4326 (2021/02/11)

Readily accessible tetraorganoborate salts undergo selective coupling reactions under blue light irradiation in the presence of catalytic amounts of transition-metal-free acridinium photocatalysts to furnish unsymmetrical biaryls, heterobiaryls and arylated olefins. This represents an interesting conceptual approach to forge C?C bonds between aryl, heteroaryl and alkenyl groups under smooth photochemical conditions. Computational studies were conducted to investigate the mechanism of the transformation.

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