90-43-7

Basic information

• Product Name: 11 -Hydroxy-2-phenylbenzene
• Synonyms: 1,1'-Biphenyl-2-ol;2-Biphenylol;2-Hydroxybiphenyl;2-hydroxydiphenyl
• CAS NO: 90-43-7
• Molecular Formula: C₁₂H₁₀O
• Molecular Weight: 170.21
• EINECS: 201-993-5
• Mol File: 90-43-7.mol
• Article Data: 199

Chemical Properties

• Melting Point: 56℃
• Boiling Point: 282 °C at 760 mmHg
• Flash Point: 140.3 °C
• Appearance: Off-white powder
• Density: 1.111 g/cm³
• Vapor Pressure: 0.00202mmHg at 25°C
• Refractive Index: 1.604
• Water Solubility: 0.7 g/L (20℃)
• CAS DataBase Reference: 11 -Hydroxy-2-phenylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 11 -Hydroxy-2-phenylbenzene(90-43-7)
• EPA Substance Registry System: 11 -Hydroxy-2-phenylbenzene(90-43-7)

Safety Data

• Hazard Codes: Xi:Irritant;; <
• Statements: R36/37/38:; R50:
• Safety Statements: S22:; S61:
• Hazardous Substances Data: 90-43-7(Hazardous Substances Data)

Usage

General Description

11-Hydroxy-2-phenylbenzene, also known as hydroxydiphenylmethane, is a chemical compound consisting of a benzene ring with a hydroxyl group attached at the 11th position and a phenyl group attached at the 2nd position. It is commonly used as a starting material in the synthesis of various pharmaceuticals, dyes, and fragrances. 11 -Hydroxy-2-phenylbenzene has been studied for its potential antioxidant and anti-inflammatory properties, making it a subject of interest in the development of new therapeutic agents. Additionally, it has been found to exhibit inhibitory effects on the growth of certain cancer cell lines, further highlighting its potential for medicinal applications. However, further research is needed to fully understand the biological activities and potential uses of 11-Hydroxy-2-phenylbenzene.

Synthetic route

2-methoxy-1,1'-biphenyl (86-26-0) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With boron tribromide In dichloromethane at 0 - 25℃;	100%
With boron tribromide In dichloromethane at -80℃;

(RS)-2-phenylcyclohexanone (1444-65-1) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With palladium chloride*2MeCN; chloranil In 1,4-dioxane at 100℃; for 18h;	100%
Multi-step reaction with 2 steps 1: dimethyl sulfoxide; oxygen; palladium(II) trifluoroacetate / acetic acid / 12 h / 80 °C / Reflux; Sealed tube 2: dimethyl sulfoxide; iodine / nitromethane / 24 h / 100 °C / Sealed tube; Green chemistry View Scheme

2-Iodophenol (533-58-4) + phenylboronic acid (98-80-6) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With potassium phosphate; SBA-Si-PEG-Pd(PPh3)n In water at 50℃; for 10h; Suzuki coupling;	99%
With palladium 10% on activated carbon; potassium carbonate In water at 20 - 80℃; for 18.5h; Suzuki-Miyaura Coupling; Inert atmosphere;	97%
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	96%

6-tert-butyl-6-phenyl-6H-dibenzo[c,e][1,2]oxasiline (1178513-84-2) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 70℃; for 5h;	99%

trimethyl(biphenyl-2-yloxy)silane (1022-21-5) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;	99%

2-Biphenylboronic acid (4688-76-0) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With oxygen; N-ethyl-N,N-diisopropylamine; [5,6]fullerene-C70 In chloroform; toluene at 20℃; for 12h; Irradiation;	98%
With N,N-dimethyl-p-toluidine N-oxide In dichloromethane at 20℃; for 0.0166667h;	95%
With tert.-butylhydroperoxide; potassium tert-butylate In water at 20 - 50℃; for 5h;	90%

dibenzofuran (132-64-9) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With sodium hydride at 190 - 192℃; for 7h;	92.5%
With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;	84%
With lithium aluminium tetrahydride; cobalt acetylacetonate; sodium t-butanolate In toluene at 140℃; for 24h; Inert atmosphere; Sealed tube;	81%

2-Bromobiphenyl (2052-07-5) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With oxygen; triethylamine; sodium iodide In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation;	91%

2-chloro-1,1'-biphenyl (2051-60-7) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; tris-(dibenzylideneacetone)dipalladium(0); cesiumhydroxide monohydrate In 1,4-dioxane at 110℃; Inert atmosphere; Glovebox; Sealed tube;	90%
With water; silica gel; copper(II) oxide at 525 - 600℃;
With water; sodium carbonate at 300 - 360℃;

(Z)-4-phenylocta-1,4,7-trien-3-one (863418-13-7) → 2-Phenylphenol (90-43-7)

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 2h;	90%

(1,1'-biphenyl)-2-yl formate → 2-Phenylphenol (90-43-7)

Conditions	Yield
With copper; Selectfluor In acetonitrile at 80℃;	90%

potassium (2-hydroxyphenyl)trifluoroborate + iodobenzene (591-50-4) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; Suzuki Coupling; Inert atmosphere; Sonication; Reflux;	89%

Diethylcarbamic acid, <1,1'-biphenyl>-2-yl ester (132939-03-8) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With zirconocene dichloride In tetrahydrofuran at 20℃; Inert atmosphere;	87%
With water; sodium hydroxide In ethanol for 8h; Reflux;	85%

dibenzothiophene sulfone (1016-05-3) → 2-Phenylphenol (90-43-7)

Conditions	Yield
Stage #1: dibenzothiophene sulfone With sodium hydroxide In water at 300℃; for 1.5h; Autoclave; Stage #2: With hydrogenchloride In water pH=7; Product distribution / selectivity;	86.5%

2-hydroxybromobenzene (95-56-7) + phenylmagnesium bromide (100-58-3) → 2-Phenylphenol (90-43-7)

Conditions	Yield
Stage #1: 2-hydroxybromobenzene; phenylmagnesium bromide With tris-(dibenzylideneacetone)dipalladium(0); 4-bromo-phenol; C30H23O2P In tetrahydrofuran at -78 - 25℃; for 2.16667h; Stage #2: With hydrogenchloride In tetrahydrofuran; water	86%
With tris-(dibenzylideneacetone)dipalladium(0); 1-bromo-4-methoxy-benzene; C30H23O2P In tetrahydrofuran at -78 - 25℃; Inert atmosphere;	96 %Spectr.

([1,1′-biphenyl]-2-yloxy)(tert-butyl)dimethylsilane (188646-07-3) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With acetyl chloride In methanol	86%

2-iodocyclohex-2-en-1-one (33948-36-6) + phenylboronic acid (98-80-6) → 2-phenylcyclohex-2-enone (4556-09-6) + 2-Phenylphenol (90-43-7)

Conditions	Yield
With palladium 10% on activated carbon; sodium carbonate In 1,4-dioxane; water at 20℃; for 24h; Suzuki-Miyaura Coupling;	A 86% B 4%

N-(phenoxy)-4-methylbenzenesulfonamide (65109-75-3) + benzene (71-43-2) → 4-Phenylphenol (92-69-3) + 2-hydroxyphenyl p-toluenesulfonimidate (65109-81-1) + toluene-4-sulfonamide (70-55-3) + 2-Phenylphenol (90-43-7)

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid for 1h; Ambient temperature; Further byproducts given;	A 14% B 13% C 85% D 29%

N-(phenoxy)-4-methylbenzenesulfonamide (65109-75-3) + benzene (71-43-2) → 4-Phenylphenol (92-69-3) + 2-hydroxyphenyl p-toluenesulfonimidate (65109-81-1) + toluene-4-sulfonamide (70-55-3) + 4-hydroxyphenyl trifluoromethanesulfonate (65109-80-0) + 2-Phenylphenol (90-43-7)

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid for 1h; Mechanism; Product distribution; Ambient temperature; other N-acyl- and N-sulfonyl-O-arylhydroxylamines under various reaction conditions, different nucleophiles;	A 14% B 13% C 85% D 3% E 29%

toluene-4-sulfonic acid,2-hydroxyphenyl ester (35616-01-4) + phenylmagnesium bromide (100-58-3) → 2-Phenylphenol (90-43-7)

Conditions	Yield
Stage #1: phenylmagnesium bromide With C24H52Cl2O12P4Pd2 In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.0833333h; Kumada-Corriu cross-coupling reaction; Inert atmosphere; Stage #2: toluene-4-sulfonic acid,2-hydroxyphenyl ester In tetrahydrofuran; 1,4-dioxane at 110℃; for 24h; Kumada-Corriu cross-coupling reaction; Inert atmosphere; chemoselective reaction;	84%

acetyl chloride (75-36-5) + 2-Phenylphenol (90-43-7) → 2-acetoxybiphenyl (3271-80-5)

Conditions	Yield
With pyridine In dichloromethane for 3h;	100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 6h; Schlenk technique; Inert atmosphere;	98%

allyl bromide (106-95-6) + 2-Phenylphenol (90-43-7) → 2-(allyloxy)-1,1'-biphenyl (20281-39-4)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 20h;	100%
With cesium fluoride In acetonitrile at 82℃;	62%
With cesium fluoride In acetonitrile at 82℃;	62%

formaldehyd (50-00-0) + 2-Phenylphenol (90-43-7) → 2-hydroxy-3-phenylbenzaldehyde (14562-10-8)

Conditions	Yield
With triethylamine; magnesium chloride In tetrahydrofuran for 3h; Heating;	100%
Stage #1: formaldehyd; 2-Phenylphenol With triethylamine; magnesium chloride In tetrahydrofuran for 1.7h; Heating / reflux; Stage #2: With hydrogenchloride In water at 0℃; pH=5;	92%
With triethylamine; magnesium chloride In tetrahydrofuran at 70℃; for 16h;	90%

propargyl bromide (106-96-7) + 2-Phenylphenol (90-43-7) → 1-phenyl-2-(2-propynyloxy)benzene (26627-30-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	100%
With potassium carbonate In acetone; toluene at 65℃; for 14h;	95%
With potassium carbonate In acetone; toluene	95%

trifluoromethylsulfonic anhydride (358-23-6) + 2-Phenylphenol (90-43-7) → biphenyl-2-yl trifluoromethanesulfonate (17763-65-4)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 2h;	100%
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	98%
With pyridine In dichloromethane at 20℃; for 2h; Inert atmosphere;	95%

2-Phenylphenol (90-43-7) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
With zinc(II) chloride; phosphorus trichloride at 20 - 180℃; for 7h;	100%
With anhydrous phosphorus trichloride; phosphorus trichloride; Zinc chloride In 5,5-dimethyl-1,3-cyclohexadiene	95%
Stage #1: 2-Phenylphenol With phosphorus trichloride at 140℃; for 5h; Inert atmosphere; Neat (no solvent); Stage #2: With zinc(II) chloride at 210℃; for 3h; Inert atmosphere; Neat (no solvent);	90%

titanium tetrachloride (7550-45-0) + 2-Phenylphenol (90-43-7) → trichloro mono(2-phenylphenoxide) titanium(IV) (263547-03-1)

Conditions	Yield
In dichloromethane byproducts: HCl; under N2; 2-phenylphenol in CH2Cl2 added to TiCl4 (molar ratio 1:1) in CH2Cl2; refluxed for 12.5 h; filtered; solvent removed; dried under vac. for 4 h; elem. anal.;	100%

titanium tetrachloride (7550-45-0) + 2-Phenylphenol (90-43-7) → [dichlorobis(2-phenylphenolate)titanium(IV)] (864720-65-0)

Conditions	Yield
In toluene byproducts: HCl; N2, vigorously refluxed for 12 h; cooled, filtered, solvent removed;	100%

phenylethylketene (20452-67-9) + 2-Phenylphenol (90-43-7) → 2-phenylphenyl 2-phenylbutanoate

Conditions	Yield
With potassium hexamethylsilazane In toluene	100%

3-phenylpentan-3-ol (1565-71-5) + 2-Phenylphenol (90-43-7) → C23H24O (1186337-44-9)

Conditions	Yield
With sulfuric acid In water for 1h; Reflux;	100%

2-Phenylphenol (90-43-7) + ortho-nitrofluorobenzene (1493-27-2) → 2-(2-nitrophenoxy)biphenyl (2688-91-7)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 95℃; for 24h;	100%
Stage #1: 2-Phenylphenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: ortho-nitrofluorobenzene In N,N-dimethyl-formamide at 20 - 50℃; for 13h; Inert atmosphere;	83%

N,N-diisopropylcarbamoyl chloride (19009-39-3) + 2-Phenylphenol (90-43-7) → [1,1'-biphenyl]-2-yl diisopropylcarbamate

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Sealed tube;	100%

[1,3]-dioxolan-2-one (96-49-1) + 2-Phenylphenol (90-43-7) → 2-(<1,1'-biphenyl>2-yloxy)ethanol (7501-02-2)

Conditions	Yield
With potassium carbonate at 160℃; for 1h; Temperature; Reagent/catalyst;	99.2%

N,N-diethylcarbamyl chloride (88-10-8) + 2-Phenylphenol (90-43-7) → Diethylcarbamic acid, <1,1'-biphenyl>-2-yl ester (132939-03-8)

Conditions	Yield
With potassium carbonate In acetonitrile for 3h; Inert atmosphere; Reflux;	99%
With potassium carbonate In acetonitrile for 7h; Heating;	95%
With potassium carbonate In acetonitrile for 8h; Reflux;

2-Phenylphenol (90-43-7) + acetone (67-64-1) → 2,2-bis-(3-phenyl-4-hydroxyphenyl)-propane (24038-68-4)

Conditions	Yield
With hydrogenchloride; 3-mercaptopropionic acid In water at 80℃; Reagent/catalyst; Inert atmosphere;	99%
With hydrogenchloride for 18h; Heating;	42%
With methanol; sulfuric acid; 1-dodecylthiol In toluene at 40℃; for 2.5h; Inert atmosphere;	9 %Chromat.

2-Phenylphenol (90-43-7) + Isopropyl isocyanate (1795-48-8) → O-2-biphenylyl N-isopropylcarbamate (417698-00-1)

Conditions	Yield
With dmap In tetrahydrofuran at 60℃; for 24h;	99%

2-Phenylphenol (90-43-7) → dibenzo[c,e][1,2]oxaborinin-6-ol (14205-96-0)

Conditions	Yield
With boron trichloride; aluminium trichloride In hexane at 70 - 75℃; for 6h;	99%
Multi-step reaction with 2 steps 1: (i) BCl3, CH2Cl2, (ii) AlCl3, PE 2: Et2O / light petroleum View Scheme
With boron trichloride

2-Phenylphenol (90-43-7) → 3-bromo[1,1’-biphenyl]-2-ol (23197-48-0)

Conditions	Yield
With N-bromo-tert-butylamine In chloroform at 0℃; Inert atmosphere;	99%
With N-Bromosuccinimide; diisopropylamine In dichloromethane for 16h; Reflux; Inert atmosphere;	96%
With N-Bromosuccinimide; diisopropylamine In dichloromethane for 16h; Inert atmosphere; Reflux;	95%

(2R,4R)-pentanediol (42075-32-1) + 2-Phenylphenol (90-43-7) → C17H20O2 (1373521-55-1)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 96h; Mitsunobu reaction;	99%

diphenyliodonium tetrafluoroborate + 2-Phenylphenol (90-43-7) → 1-methoxy-3-phenoxybenzene (1655-68-1)

Conditions	Yield
Stage #1: 2-Phenylphenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: diphenyliodonium tetrafluoroborate In tetrahydrofuran at 20℃; for 3h;	99%

bis(2-methylphenyl)iodonium tetrafluoroborate + 2-Phenylphenol (90-43-7) → 1-(3-methoxyphenoxy)-2-methylbenzene (23951-29-3)

Conditions	Yield
Stage #1: 2-Phenylphenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: bis(2-methylphenyl)iodonium tetrafluoroborate In tetrahydrofuran at 40℃; for 0.5h;	99%

2-Phenylphenol (90-43-7) + N,N`-sulfuryldiimidazole (7189-69-7) → (1,1'-biphenyl)-2-yl 1H-imidazole-1-sulfonate

Conditions	Yield
With caesium carbonate In tetrahydrofuran	99%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;	98%

4-tert-Butylcatechol (98-29-3) + 4-(4-chlorophenoxy)-3,5,6-trifluorophthalonitrile + 2-Phenylphenol (90-43-7) → C36H25ClN2O4

Conditions	Yield
Stage #1: 4-tert-Butylcatechol; 4-(4-chlorophenoxy)-3,5,6-trifluorophthalonitrile With potassium carbonate In acetonitrile at 80℃; for 2h; Stage #2: 2-Phenylphenol With potassium carbonate In acetonitrile at 80℃; for 10h;	99%

1-iodo-butane (542-69-8) + carbon monoxide (201230-82-2) + 2-Phenylphenol (90-43-7) → valeric acid biphenyl-2-yl ester (854880-18-5)

Conditions	Yield
With rhodium(III) chloride; 1,3-bis-(diphenylphosphino)propane; sodium carbonate; sodium bromide In 1,4-dioxane at 120℃; under 750.075 Torr; for 24h; Inert atmosphere; chemoselective reaction;	99%

sodium benzenesulfonate (873-55-2) + 2-Phenylphenol (90-43-7) → [1,1’-biphenyl]-2-yl benzenesulfonate (21419-72-7)

Conditions	Yield
In water; acetonitrile at 20℃; for 2h; Electrochemical reaction;	99%

Upstream product

• 515-42-4 sodium phenylsulfonate 
• 5409-83-6 2,8-dichlorodibenzofuran 
• 93-99-2 benzoic acid phenyl ester 
• 1985-99-5 6-hydroxy-biphenyl-2-carboxylic acid 
• 2051-60-7 2-chloro-1,1'-biphenyl 
• 533-58-4 2-Iodophenol 
• 1124-19-2 phenyltin trichloride 
• 626-02-8 3-Iodophenol 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 108-95-2 phenol 
• 1502-22-3 2-(1-cyclohexenyl)cyclohexanone 
• 64908-64-1 2-phenoxyisoindol-1,3-dione 
• 71-43-2 benzene 

Downstream Products

• 102806-25-7 2-(benzyloxy)-1,1′-biphenyl 
• 5449-49-0 [1,1'-biphenyl]-2-yl benzoate 
• 607-07-8 1,2-bis(2-biphenylyloxy)ethane 
• 3245-43-0 1-(2-bromoethoxy)-2-phenylbenzene 
• 6738-04-1 2-phenoxy-1,1'-biphenyl 
• 35664-61-0 o-(2,2-Dimethoxyethoxy)biphenyl 
• 121233-18-9 (2,6-Bis-<2-phenyl-phenoxy>-benzol)-<1-azo-1>-naphthol-(2) 
• 85-97-2 2-chloro-6-phenylphenol 
• 607-12-5 5-chloro-biphenyl-2-ol 
• 5335-24-0 2,4-dichloro-6-phenylphenol 
• 6531-86-8 2-cyclohexylcyclohexanol 
• 1444-64-0 2-phenylcyclohexanol 
• 105343-65-5 3,5,4'-tribromo-biphenyl-2-ol 
• 55815-20-8 3,5-dibromo-2-hydroxybiphenyl 

Relevant articles and documents

Pd(II) complexes with ONN pincer ligand: Tailored synthesis, characterization, DFT, and catalytic activity toward the Suzuki-Miyaura reaction

A pincer type ONN tridentate Schiff base ligand, 2-(((pyridin-2-yl)methylimino)methyl)-6-methoxyphenol, (L1) synthesized by the condensation of 4-hydroxy-3-methoxy-benzaldehyde and (pyridin-2-yl)methanamine. The ligand L1 and the new Pd(II) heteroleptic complexes of the composition [Pd(L1)(L2)]Cl, where L2 = benzimidazole, imidazole, benzooxazol or pyridine were synthesized and characterized by a set of chemical, spectrometric and spectroscopic analyses. These complexes were named 1 to 4, respectively. The FT-IR and DFT have suggested that ligand is coordinated with metal through azomethine-N and phenolic-O and arranged in square planar fashion around the metal. Correlation coefficients value between 0.995 - 0.993 shows satisfactory agreement in theoretical and experimental 1H-NMR and 13C-NMR. Benzimidazole anchored complex 1 exhibits an excellent catalytic activity. DFT calculated the energy profile diagram of the Suzuki-Miyaura reaction.

Microflowers formed by complexation-driven self-assembly between palladium(ii) and bis-theophyllines: Immortal catalyst for C-C cross-coupling reactions

The Pd catalyst for Suzuki-Miyaura or the other C-C coupling reactions is one of the central tools in organic synthesis related to medicine, agricultural chemicals and advanced materials. However, recycling palladium is a bottleneck for developing the extreme potential of Pd in chemistry. Herein, we established a new heterogeneous Pd catalytic system in which the catalyst is a nanopetal-gathered flower-like microsphere self-assembled from PdCl2 and alkyl-linked bis-theophyllines. The microflowers catalyzed quantitatively the reaction of aryl bromides and phenylboronic acid in aqueous media at room temperature. It was found that the reaction proceeds better in an air atmosphere than in nitrogen gas even though the Pd(ii) species employed was lowered to 0.001 mol% in the substance. Very interestingly, the microflowers could be recycled 20 times without deactivation in the C-C coupling reaction between bromobenzene and phenylboronic acid in the presence of sodium chloride. We found that the sodium chloride added played an important role in maintaining the morphology of microflowers and preventing the formation of metallic Pd particles.

C(acyl)-C(sp2) and C(sp2)-C(sp2) Suzuki-Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes

Application of N-heterocyclic carbene (NHC) palladium complexes has been successful for the modulation of C-C coupling reactions. For this purpose, a series of azolium salts (1a-f) including benzothiazolium, benzimidazolium, and imidazolium, bearing a CN-substituted benzyl moiety, and their (NHC)2PdBr2 (2a-c) and PEPPSI-type palladium (3b-f) complexes have been systematically prepared to catalyse acylative Suzuki-Miyaura coupling reaction of acyl chlorides with arylboronic acids to form benzophenone derivatives in the presence of potassium carbonate as a base and to catalyse the traditional Suzuki-Miyaura coupling reaction of bromobenzene with arylboronic acids to form biaryls. All the synthesized compounds were fully characterized by Fourier Transform Infrared (FTIR), and 1H and 13C NMR spectroscopies. X-ray diffraction studies on single crystals of 3c, 3e and 3f prove the square planar geometry. Scanning Electron Microscopy (SEM), energy dispersive X-ray spectroscopy (EDS), metal mapping analyses and thermal gravimetric analysis (TGA) were performed to get further insights into the mechanism of the Suzuki-Miyaura cross coupling reactions. Mechanistic studies have revealed that the stability and coordination of the complexes by the CN group are achieved by the removal of pyridine from the complex in catalytic cycles. The presence of the CN group in the (NHC)Pd complexes significantly increased the catalytic activities for both reactions.