4316-51-2

Usage

Chemical Properties

White solid

InChI:InChI=1/C19H17NO/c1-21-19-14-12-18(13-15-19)20(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-15H,1H3

Synthetic route

4-chloromethoxybenzene (623-12-1) + diphenylamine (122-39-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 80℃; for 12h;	99%
With bis(η3-allyl-μ-chloropalladium(II)); 2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine); sodium t-butanolate In dodecane; toluene at 100℃; for 6h; Catalytic behavior; Reagent/catalyst; Glovebox;	99%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 70℃; for 16h;	97%

1-bromo-4-methoxy-benzene (104-92-7) + diphenylamine (122-39-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With potassium hydroxide; bis(tri-tert-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 6h;	99%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;	99%
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In toluene at 50℃;	97%

para-iodoanisole (696-62-8) + diphenylamine (122-39-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With copper(l) iodide; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; sodium t-butanolate In toluene at 110℃; for 40h; post-Ullmann reaction;	96%
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium hydroxide In dimethyl sulfoxide at 120℃; for 3h;	96%
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In toluene at 30℃;	93%

bromobenzene (108-86-1) + 4-methoxy-aniline (104-94-9) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With dichloro{1,10-[di-(2-diizopropylaminoethyl)]-3,3'-o-xylyldibenzimidazolidin-2,2'-diylidene}palladium (II); potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Buchwald-Hartwig amination; Inert atmosphere;	95%
With (6-Dipp)PdCl2-SPhos; sodium t-butanolate In neat (no solvent) at 110℃; for 24h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere;	90%
With potassium hydroxide In water for 24h; Buchwald-Hartwig reaction; Reflux; Inert atmosphere;	85%

iodobenzene (591-50-4) + 4-methoxy-aniline (104-94-9) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With [2,2]bipyridinyl; potassium tert-butylate; copper(l) iodide In toluene at 115℃; for 3.5h;	94%
With tetraethoxy orthosilicate; caesium carbonate; copper(l) iodide at 145℃; for 38h; Ullmann coupling reaction;	85%
With C39H33CuF3N2P2(1+)*ClO4(1-); potassium tert-butylate In toluene at 90℃; for 12h; Inert atmosphere;	80%

1-bromo-4-methoxy-benzene (104-92-7) + N-(trimethylsilyl)-diphenylamine (17425-91-1) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Inert atmosphere;	94%
With cesium fluoride; bis(dibenzylideneacetone)-palladium(0); XPhos at 100℃; for 1h; Time; Reagent/catalyst; Inert atmosphere;	94%
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene hydrochloride; potassium tert-butylate; cesium fluoride at 100℃; for 36h; Inert atmosphere;	67%

4-methoxy-aniline (104-94-9) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 72h;	90%

bromobenzene (108-86-1) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With C46H58Br2N4O10Pd; potassium tert-butylate In 1,2-dimethoxyethane at 80℃; for 15h; Inert atmosphere; Buchwald-Hartwig amination;	A 11% B 89%
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 135℃; for 10.5h; high pressure;	A 2% B 86%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux;	A 41% B 45%

4-methoxy-aniline (104-94-9) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 10h;	A 89% B 4%

4-methoxy-aniline (104-94-9) + chlorobenzene (108-90-7) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With potassium tert-butylate; copper(l) iodide; tributylphosphine In toluene at 135℃; for 10.5h; high pressure;	A 3% B 85%

4-methoxy-aniline (104-94-9) + chlorobenzene (108-90-7) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; (E)-2-(((2,5-bis(trifluoromethyl)phenyl)imino)methyl)phenol; sodium t-butanolate In o-xylene at 145℃; for 12h; Schlenk technique; Inert atmosphere;	85%

iodobenzene (591-50-4) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With potassium tert-butylate; copper(l) iodide In toluene at 135℃; for 14h;	A 12% B 82%
With copper(l) iodide; cesium fluoride In dimethyl sulfoxide at 130℃; for 24h; Ullmann Condensation; Inert atmosphere; Glovebox;	A 37 %Chromat. B 15%

para-iodoanisole (696-62-8) + N-phenyl-1-naphthylamine (90-30-2) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
potassium hydroxide; copper In various solvent(s) at 160℃; for 5h;	79%

bromobenzene (108-86-1) + N-(4-methoxyphenyl)phenylamine (1208-86-2) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Stage #1: bromobenzene With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: N-(4-methoxyphenyl)phenylamine With sodium t-butanolate In toluene at 90℃; for 20h; Hartwig-Buchwald coupling;	79%
With C37H50BrO3PPd In 1,4-dioxane at 80℃; Kinetics; Inert atmosphere; Glovebox; Sealed tube;

N-(4-methoxyphenyl)phenylamine (1208-86-2) + triphenylbismuth(V) diacetate (28899-97-0) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
copper In dichloromethane for 72h; Ambient temperature;	78%

triphenylbismuth(V) diacetate (28899-97-0) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
copper In dichloromethane for 24h; Ambient temperature;	A 28% B 68%

para-methoxynitrobenzene (100-17-4) + diphenylamine (122-39-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With potassium phosphate; bis(acetylacetonato)palladium(II); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In n-heptane at 130℃; for 24h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;	66%
With potassium phosphate; bis(acetylacetonato)palladium(II); BrettPhos In n-heptane at 130℃; for 24h;	66%
With bis(acetylacetonato)palladium(II); tripotassium phosphate "n" hydrate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In n-heptane at 130℃; for 24h; Inert atmosphere;	61%

4-Methoxyphenyl isocyanate (5416-93-3) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With cesium fluoride In acetonitrile at 100℃; for 14h; Inert atmosphere;	46%

Diphenyliodonium triflate (66003-76-7) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Stage #1: Diphenyliodonium triflate; 4-methoxy-aniline With copper(l) iodide; 2,6-di-tert-butyl-pyridine In toluene at 20℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With copper(l) iodide; 1,10-Phenanthroline; potassium tert-butylate In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;	A 5% B 44%

1.4-dibromobenzene (106-37-6) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 110℃; Hartwig-Buchwald coupling; Inert atmosphere;	A 42% B 9%

4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Product distribution; effect of amount of Ph3Bi(OAc)2 and reaction time;

1-bromo-4-methoxy-benzene (104-92-7) + diphenylamine (122-39-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2) + N-(3-methoxyphenyl)-diphenylamine (20588-62-9)

Conditions	Yield
With potassium hydroxide; PEGDM-400 In toluene at 158 - 161℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With iron(III) oxide; potassium tert-butylate In dimethyl sulfoxide at 130℃; for 36h; regioselective reaction;

iodobenzene (591-50-4) + para-iodoanisole (696-62-8) + diphenylamine (122-39-4) → N,N-diphenylaminobenzene (603-34-9) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
potassium hydroxide; copper at 160℃; Rate constant; Mechanism; competitive reaction, var. catalysts;

iodobenzene (591-50-4) + para-methoxynitrobenzene (100-17-4) → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
With copper at 195℃;

bromobenzene (108-86-1) + ς-[2,4,6-(CH3)3C6H2]Ni(2,2'-bipyridyl)Br → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 3 h / 90 °C 2: 99 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 6 h / 90 °C View Scheme

aniline (62-53-3) + 5-(4-formyl-3,5-dimethoxyphenoxy)valeric aldehyde linker on a polyethylene glycol resin → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 3 h / 90 °C 2: 99 percent / KOH; Pd[P(t-Bu3)]2; cetyltrimethylammonium bromide / toluene; H2O / 6 h / 90 °C View Scheme

bromobenzene (108-86-1) + NO2, Br2 → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 1 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme

aniline (62-53-3) + Wang resin-bound styrene 4 → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 1 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: 75 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 25 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme

chlorobenzene (108-90-7) + SOCl2 → N,N-diphenyl-4-methoxyaniline (4316-51-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 25 h / Ambient temperature 2: 97 percent / Pd(dba)2, P(t-Bu)3, t-BuONa / toluene / 16 h / 70 °C View Scheme

N,N-diphenyl-4-methoxyaniline (4316-51-2) → 4-hydroxyltriphenylamine (25069-86-7)

Conditions	Yield
Stage #1: N,N-diphenyl-4-methoxyaniline With boron tribromide In dichloromethane; chloroform at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: With methanol In dichloromethane; chloroform Inert atmosphere; Cooling with ice;	100%
Stage #1: N,N-diphenyl-4-methoxyaniline With boron tribromide In dichloromethane at 0 - 20℃; for 24.5h; Stage #2: With water In dichloromethane	99%
With boron tribromide In dichloromethane at 20℃; for 3h;	90%

N,N-diphenyl-4-methoxyaniline (4316-51-2) → 4,4′-dibromo-4′′-methoxytriphenylamine (100308-69-8)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 3h;	95%
With N-Bromosuccinimide

N,N-diphenyl-4-methoxyaniline (4316-51-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-[N-phenyl-N-(4-methoxyphenyl)amino]benzaldehyde (87755-82-6)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane for 4h; Vilsmeier formylation; Inert atmosphere; Reflux;	94%
With trichlorophosphate at 0 - 80℃; for 1h; Inert atmosphere;	94.8%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.75h; Vilsmeier-Haack Formylation; Stage #2: N,N-diphenyl-4-methoxyaniline at 60℃; for 2h; Vilsmeier-Haack Formylation;	85%

N,N-diphenyl-4-methoxyaniline (4316-51-2) + trimethylaluminum (75-24-1) → diphenyl(p-tolyl)amine (4316-53-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In toluene at 100℃; for 6h; Sealed tube; Glovebox; Inert atmosphere;	87%

N,N-diphenyl-4-methoxyaniline (4316-51-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C25H28BNO3

Conditions	Yield
With C26H45OSiY In hexane at 100℃; for 24h; regioselective reaction;	83%

N,N-diphenyl-4-methoxyaniline (4316-51-2) → 4,4-diiodo-4''-methoxytriphenylamine (199297-07-9)

Conditions	Yield
With potassium iodate; potassium iodide In water; acetic acid at 80℃; for 3h; Iodination;	82%
With potassium iodate; potassium iodide In acetic acid
With potassium iodate; potassium iodide In acetic acid

N,N-diphenyl-4-methoxyaniline (4316-51-2) + para-methylphenylmagnesium bromide (4294-57-9) → 4'-methyl-N,N-diphenyl-[1,1'-biphenyl]-4-amine

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); C23H28N4 In tetrahydrofuran; m-xylene at 60℃; for 4h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube;	81%

N,N-diphenyl-4-methoxyaniline (4316-51-2) + acetyl chloride (75-36-5) → C21H19NO2

Conditions	Yield
With zinc(II) chloride In dichloromethane	80%

1,1-diphenyl-4-(p-di-n-propylaminophenyl)-1,3-butadiene + N,N-diphenyl-4-methoxyaniline (4316-51-2) → 4,4’-bisformyl-4’’-methoxytriphenylamine (149676-16-4)

Conditions	Yield
	76.5%

N,N-diphenyl-4-methoxyaniline (4316-51-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4,4’-bisformyl-4’’-methoxytriphenylamine (149676-16-4)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane at 0℃; for 15h; Vilsmeier-Haack Formylation; Inert atmosphere; Reflux;	75%
With trichlorophosphate at 95℃; for 4h; Inert atmosphere;	71%
With trichlorophosphate In 1,2-dichloro-benzene at 85℃; for 24h; Vilsmeyer reaction;	67%
With trichlorophosphate In 1,2-dichloro-ethane for 6h; Reflux;	36.7%
With trichlorophosphate at 80℃; for 24h; Vilsmeier-Haack Formylation;

1-Methylbenzimidazole (1632-83-3) + N,N-diphenyl-4-methoxyaniline (4316-51-2) → 4-(1-methyl-1H-benzimidazol-2-yl)-N,N-diphenylbenzenamine (1542275-72-8)

Conditions	Yield
With ortho-tolylmagnesium bromide; bis(1,5-cyclooctadiene)nickel (0); C23H30N4 In m-xylene at 90℃; for 16h;	75%

N,N-diphenyl-4-methoxyaniline (4316-51-2) → 4-(N-phenyl-N-(4-methoxy)phenylamino)-1-bromobenzene (949910-86-5)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 5h;	75%

N,N-diphenyl-4-methoxyaniline (4316-51-2) → N4,N4'-bis(4-methoxyphenyl)-N4,N4'-diphenyl-4,4'-diaminobiphenyl (20441-07-0)

Conditions	Yield
Stage #1: N,N-diphenyl-4-methoxyaniline With methanesulfonic acid In dichloromethane at 0℃; Stage #2: With chloranil In dichloromethane at 0 - 20℃; for 3h;	66%
With tetrafluoroboric acid diethyl ether; C22H42N12*2BF4(1-)*2H(1+) In acetonitrile at 20℃; Reagent/catalyst; Cooling with ice;	90 %Spectr.

Upstream product

• 696-62-8 para-iodoanisole 
• 122-39-4 diphenylamine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 591-50-4 iodobenzene 
• 100-17-4 para-methoxynitrobenzene 
• 104-94-9 4-methoxy-aniline 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 108-86-1 bromobenzene 
• 17425-91-1 N-(trimethylsilyl)-diphenylamine 
• 66003-76-7 Diphenyliodonium triflate 
• 108-90-7 chlorobenzene 
• 90-30-2 N-phenyl-1-naphthylamine 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 199297-07-9 4,4-diiodo-4''-methoxytriphenylamine 
• 149676-16-4 4,4’-bisformyl-4’’-methoxytriphenylamine 
• 100308-69-8 4,4′-dibromo-4′′-methoxytriphenylamine 
• 1374356-15-6 3-chloro-6-[4-(diphenylamino)phenoxy]-1,2,4,5-tetrazine 
• 1374356-20-3 3,6-bis[4-(diphenylamino)phenoxy]-1,2,4,5-tetrazine 
• 19264-74-5 9-(4-methoxyphenyl)-9H-carbazole 
• 1417618-07-5 3-methoxy-9-phenyl-9H-carbazole 
• 36809-17-3 4-phenoxytriphenylamine 
• 521950-74-3 4-[N-(4-methoxyphenyl)-N-phenylamino]benzyl alcohol 
• 1351663-33-6 diethyl 4-[N-(4-methoxyphenyl)-N-phenylamino]benzylphosphonate 

Relevant academic research and scientific papers

TRIARYL PHOSPHINE LIGANDS, PREPARATION METHOD THEREFOR, AND USE IN CATALYSING COUPLING REACTIONS

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The invention relates to a triptycene carbene allyl palladium compound and application thereof. The structural formula of the triptycene carbene allyl palladium compound is a formula I or a fotmula II. Compared with a conventional metal palladium catalyst, the triptycene carbene allyl palladium compound is easy and convenient to prepare, high in yield and suitable for various substrates, the use amount of a catalyst can be reduced to one ten thousandth, and the compound has a good catalytic effect on various metal palladium catalytic reactions. The compound has important application value for researching the progress and application of catalytic reaction.

Triptycene carbene palladium pyridine complex and application thereof

The invention relates to a triptycene carbene palladium pyridine complex and application thereof. The structural formula of the triptycene carbene palladium pyridine complex is shown as a formula I. The complex provided by the invention is correct in detection. Based on the defects that a metal catalyst used for organic reaction at the present stage cannot be suitable for various substrates, the catalyst in use amount and cost and is difficult to preserve for a long time, the invention provides the triptycene carbene palladium pyridine complex used as a catalyst, wherein the preparation is simple and convenient, the yield is high, the triptycene carbene palladium pyridine complex is suitable for various substrates, the usage amount of the catalyst can be reduced to one ten thousandth, and the triptycene carbene palladium pyridine complex has a better catalytic effect on various metal palladium catalytic reactions. The triptycene carbene palladium pyridine complex has important application value for researching the progress and application of catalytic reaction.

Triptycene carbene tridentate metal coordination compound and application thereof

The invention relates to a triptycene carbene tridentate metal coordination compound, wherein the structural formula of the triptycene carbene tridentate metal coordination compound is shown in the specification. According to the invention, the compound is correct in detection; based on the problems that a metal catalyst used in an organic reaction at the present stage cannot be suitable for various substrates, the catalyst content is high, the cost is high, long-time storage is difficult, and the like, the triptycene carbene tridentate metal coordination compound provided by the invention is used as a catalyst, the preparation is simple and convenient, the yield is high, the triptycene carbene tridentate metal coordination compound is suitable for various substrates, the usage amount of the catalyst can be reduced to one ten thousandth, and the triptycene carbene tridentate metal coordination compound has a better catalytic effect on various metal catalytic reactions, and has important application value for researching the progress and application of catalytic reaction.

DIARYL AMINE COMPOUND AND METHOD FOR PRODUCING THE SAME

The present invention relates to a process for the preparation of diaryl amine compounds. A compound represented by chemical formula 1, a compound represented by chemical formula 2, and a synthetic reagent in a solvent, the synthetic reagent being CsF, KF, 18 - crown -6, K. 2 CO3, [TBAT] The present invention relates to a process for the preparation of diaryl amine compounds comprising a material selected from the group consisting of a (tetrabutylammonium difluorotriphenylsilicate), TBAF (tetrabutylammonium fluoride) and combinations thereof. Chemical Formula 1. Chemical Formula 2. The diaryl amine compound can be synthesized under the absence of a transition metal to be used to synthesize diaryl amine compounds having various substituents.

A Polystyrene-Cross-Linking Tricyclohexylphosphine: Synthesis, Characterization and Applications to Pd-Catalyzed Cross-Coupling Reactions of Aryl Chlorides

A polystyrene-cross-linking tricyclohexylphosphine (PS-TCP) was synthesized through radical emulsion polymerization of 4-tert-butylstyrene as a monomer and tris(trans-4-styrylcyclohexyl)phosphine as a threefold cross-linker. The PS-TCP showed enhanced ligand performance compared to the corresponding polystyrene-triphenylphosphine hybrid PS-TPP and tricyclohexylphosphine in Pd-catalyzed Suzuki–Miyaura and Buchwald–Hartwig reactions of aryl chlorides.

Systematic Control of the Overlapping Energy Region for an Efficient Intramolecular Energy Transfer: Functionalized Salen-Al/Triphenylamine Guest-Host Assemblies

A series of triphenylamine (TPA)-containing salen-Al assembly dyads, [salen(3-tBu-5-R)2Al(OC6H4-p-N(C6H5)2)] [salen = N,N′-bis(salicylidene)ethylenediamine; R = H (D1), tBu (D2), Ph (D3), OMe (D4), and NMe2 (D5)], were prepared in good yield (50-80%) and fully characterized by NMR spectroscopy and elemental analysis. Both the UV/vis absorption and photoluminescence (PL) spectra of D1-D4, except for D5, in a tetrahydrofuran solution exhibited dual patterns, which are assignable to the salen-Al-centered α-α? transition (low-energy region) and the TPA-centered α-α? transition (high-energy region). In particular, the emission spectra of the dyads displayed interesting dual-emissive patterns via a significant intramolecular energy transfer (IET) process between the salen-Al moiety and TPA group. Notably, this IET process was systematically tuned by varying the substituents and dominantly observed in the rigid state. More interestingly, compared to the salen-Al complexes (A1-A4) without the TPA group, D1-D4 exhibited enhanced quantum efficiencies. Time-dependent density functional theory calculations on the S1-optimized structures of D1-D5 further supported these experimental results by indicating the existence of independent transition states between the salen-Al moiety and TPA group in the assembly dyads. The present study reports the first example of salen-Al complexes bearing electron-rich TPA moieties.