13716-12-6

Basic information

• Product Name: Tri-tert-butylphosphine
• Synonyms: Phosphine, tris(1,1-dimethylethyl)-;TRI-TERT-BUTYL-PHOSPHANE;TRI-TERT-BUTYLPHOSPHINE;TRI-T-BUTYLPHOSPHINE;tris(1,1-dimethylethyl)phosphine;TRI-TERT-BUTYLPHOSPHINE, 1M IN TOLUENE;TRI-TERT-BUTYLPHOSPHINE, TECH., 90%;TERT-BUTYLPHOSPHINE, ELEC. GR., 99.9995%
• CAS NO: 13716-12-6
• Molecular Formula: C₁₂H₂₇P
• Molecular Weight: 202.32
• EINECS: 237-266-4
• Product Categories: Phosphines;pharmacetical;Ligand;API intermediates;Mitsunobu Reaction;Phosphine Ligands;Phosphines (Mitsunobu Reaction);Synthetic Organic Chemistry;Basic Phosphine LigandsCatalysis and Inorganic Chemistry;Catalysis and Inorganic Chemistry;Cross-Coupling;Phosphine Ligands;Phosphorus Compounds;organophosphorus ligand;organophosphine ligand;OLED materials,pharm chemical,electronic;Achiral Phosphine;Alkyl Phosphine
• Mol File: 13716-12-6.mol

Chemical Properties

• Melting Point: 30-35 °C(lit.)
• Boiling Point: 102-103 °C13 mm Hg(lit.)
• Flash Point: 1 °F
• Appearance: /solid
• Density: 0.861 g/mL at 25 °C
• Vapor Pressure: 0.105mmHg at 25°C
• Storage Temp.: Flammables area
• Water Solubility: insoluble
• Sensitive: Air & Moisture Sensitive
• BRN: 1738613
• CAS DataBase Reference: Tri-tert-butylphosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Tri-tert-butylphosphine(13716-12-6)
• EPA Substance Registry System: Tri-tert-butylphosphine(13716-12-6)

Safety Data

• Hazard Codes: F,C
• Statements: 17-34-67-65-63-48/20-11
• Safety Statements: 26-45-62-36/37/39-25-43-27-16
• RIDADR: UN 2846 4.2/PG 1
• WGK Germany: 3
• F: 10-19-23
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 13716-12-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Tri-tert-butylphosphine is used as a valuable ligand for several coupling reactions in the chemical synthesis industry. Its role in the preparation of phosphine ligands for metal complexes makes it a crucial component in the production of various chemical compounds.
Used in Catalytic Asymmetric Hydrogenations:
In the field of asymmetric hydrogenations, Tri-tert-butylphosphine is used as a ligand for metal complexes, enabling the selective formation of chiral products with high enantioselectivity and efficiency.
Used in Asymmetric Reactions:
Tri-tert-butylphosphine is employed as a ligand in various asymmetric reactions, contributing to the development of enantiomerically pure compounds, which are essential in the pharmaceutical and agrochemical industries.
Used in Transition Metal Coupling Reactions:
This reagent is used as a ligand in transition metal coupling reactions, facilitating the formation of carbon-carbon and carbon-heteroatom bonds, which are vital in the synthesis of complex organic molecules.
Used in Catalytic Polymerization:
Tri-tert-butylphosphine is used in the preparation of other phosphines that act as catalysts in polymerization reactions, leading to the production of various polymers with specific properties and applications.
Used in Convenient Handling:
The product is offered as a THF (tetrahydrofuran) solution, which provides more convenient handling and improved safety during the synthesis process. This form of the reagent is particularly useful in research and development settings, as well as in industrial applications where ease of use and safety are paramount.

Reaction

Useful as a ligand in a variety of palladium-catalyzed C-N, C-O and C-C bond-forming reactions under mild conditions.

InChI:InChI=1/C12H27P/c1-10(2,3)13(11(4,5)6)12(7,8)9/h1-9H3

Synthetic route

t-butyl bromide (507-19-7) → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
With calcium phosphide; nickel(II) acetylacetonate In tetrahydrofuran at 70℃; for 10h; Temperature; Inert atmosphere;	95%

di(tert-butyl)chlorophosphine (13716-10-4) + tert-butylmagnesium chloride (677-22-5) → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
copper(l) chloride In tetrahydrofuran at 20 - 40℃; for 4h;	90.2%
copper(l) chloride In tetrahydrofuran at 20 - 40℃; for 4h; Quantum yield;	54.4%
copper(l) chloride In tetrahydrofuran at 20℃; for 11h; Conversion of starting material; Heating / reflux;

tert-butylmagnesium chloride (677-22-5) + phosphorus trichloride (7719-12-2, 52843-90-0) → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
With lithium bromide; copper(l) iodide In diethyl ether; hexane at -20 - 20℃; for 4h;	88.3%

bis(tri-tert-butylphosphine)platinum(0) (60648-70-6) + bis(pentamethylcyclopentadienyl)dizinc (849926-75-6, 773895-85-5) → tri-tert-butyl phosphine (13716-12-6) + Pt(Zn(pentamethylcyclopentadienyl))6

Conditions	Yield
In benzene at 25℃; for 0.333333h; Schlenk technique; Glovebox; Inert atmosphere;	A n/a B 30%

tert-butylmagnesium chloride (677-22-5) → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
With phosphorus trichloride

di(tert-butyl)chlorophosphine (13716-10-4) + tert.-butyl lithium (594-19-4) → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
In pentane

Tri-tert-butylphosphantellurid (60483-74-1) + tertiary butyl arsine (39760-34-4) → tri-tert-butyl phosphine (13716-12-6) + telluro-tri-t-butylarsorane

Conditions	Yield
In benzene

tert.-butyl lithium (594-19-4) + tri(t-butyl)(methyltelluro)phosphoniumiodid → tri-tert-butyl phosphine (13716-12-6) + di-tert-butyl-tellurium (83817-35-0)

2,2',3,3'-Tetra-tert-butyl-1,1'-bicyclotriphosphan (93646-62-9) → tri-tert-butyl phosphine (13716-12-6) + 2,3,4,6-tetra-tert-butylbicyclo<3.1.0>hexaphosphane (79593-41-2) + 2,2',3,3',4,4'-hexa-tert-butyl-1,1'-bicyclotetraphosphane (77256-90-7, 145678-98-4)

Conditions	Yield
at 128℃;

methyldi-t-butylphosphine (6002-40-0) + C32H12BF24(1-)*C12H27P*H(1+) → tri-tert-butyl phosphine (13716-12-6) + C32H12BF24(1-)*C9H21P*H(1+)

Conditions	Yield
In tetrahydrofuran at 20℃; Equilibrium constant;

tri-t-butylphosphonium tetraphenylborate complex + tricyclohexylphosphine (2622-14-2) → tri-tert-butyl phosphine (13716-12-6) + tricyclohexylphosphonium tetraphenylborate

Conditions	Yield
In tetrahydrofuran at 20℃; Equilibrium constant;

C32H12BF24(1-)*C12H27P*H(1+) + tricyclohexylphosphine (2622-14-2) → tri-tert-butyl phosphine (13716-12-6) + C32H12BF24(1-)*C18H33P*H(1+)

Conditions	Yield
In tetrahydrofuran at 20℃; Equilibrium constant;

bromobenzene (108-86-1) + Pd[P(t-Bu)3]2 → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
In benzene-d6 at 70℃; Equilibrium constant;

iodobenzene (591-50-4) + Pd[P(t-Bu)3]2 → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
In benzene-d6 at 70℃; Equilibrium constant;

ortho-methylphenyl iodide (615-37-2) + Pd[P(t-Bu)3]2 → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
In benzene-d6 at 70℃; Equilibrium constant;

2-methylchlorobenzene (95-49-8) + Pd[P(t-Bu)3]2 → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
In benzene-d6 at 70℃; Equilibrium constant;

2-methylphenyl bromide (95-46-5) + Pd[P(t-Bu)3]2 → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
In benzene-d6 at 70℃; Equilibrium constant;

tert.-butyl lithium (594-19-4) → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
With phosphorus trichloride

tBu3P(CO2)B(C6F5)3 → tri-tert-butyl phosphine (13716-12-6) + carbon dioxide (124-38-9) + tris(pentafluorophenyl)borate (1109-15-5)

Conditions	Yield
80°C, vac.;

(C6F5)2BOB(C6F5)2OC(O)P(C(CH3)3)3 → tetrakis(pentafluorophenyl)diboroxane (262607-62-5) + tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
In not given purging with N2 at room temp.;

[Fe(NCtBu2)4] → tert-butyl isocyanide (630-18-2) + tri-tert-butyl phosphine (13716-12-6) + [Fe2(NCtBu2)5]

Conditions	Yield
With phosphorus In benzene-d6 at 50℃; for 29h; Inert atmosphere;

tris(tert-butyl)phosphine sulfide (7441-04-5) → tri-tert-butyl phosphine (13716-12-6)

Conditions	Yield
With Raney-Ni In ethanol; benzene at 20℃; for 0.333333h; Inert atmosphere;	97 %Spectr.

[Pd(κ2P,C-PtBu2CMe2CH2)(PtBu3)][B((3,5-CF3)2C6H3)4] → bis(tri-t-butylphosphine)palladium(0) (53199-31-8) + tri-tert-butyl phosphine (13716-12-6) + palladium (7440-05-3)

Conditions	Yield
With hydrogen at 20℃; under 750.075 Torr; for 40h;

tri-tert-butyl phosphine (13716-12-6) → Tri(tert.-butyl)difluorphosphoran (29149-35-7)

Conditions	Yield
With xenon difluoride In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;	100%
With Carbonyl fluoride In dichloromethane at 25℃; for 12h;	75%
With iodine pentafluoride In acetonitrile at -25℃;	22.4%
With antimony(III) fluoride

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (425378-68-3) + tri-tert-butyl phosphine (13716-12-6) + 2-bromo-5-fluorobenzonitrile (57381-39-2) → 4,2'-difluoro-5'-nitrobiphenyl-2-carbonitrile (425378-81-0) + 4,2'-difluoro-5'-[3-(1-fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile (425377-62-4)

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; 1,4-dioxane; water	A n/a B 100%

tert-butyl 5-bromoindoline-1-carboxylate (261732-38-1) + tri-tert-butyl phosphine (13716-12-6) + argon → 2-phenylaniline (90-41-5)

Conditions	Yield
With caesium carbonate In 1,4-dioxane; diethyl ether; hexane; ethyl acetate	100%

tri-tert-butyl phosphine (13716-12-6) + [Au2(S-tBu)(P(t-Bu)3)2][BF4] (1126245-74-6) → bis(tri-t-butylphosphine)gold(I) tetrafluoroborate (168000-65-5) + gold(I)(StBu)(PtBu3) (1126245-88-2)

Conditions	Yield
In dichloromethane; toluene (N2 or Ar); Au complex in CH2Cl2 added to toluene soln. of 2 equiv. of PtBu3, stirred for 1 h; added dropwise to pentane, ppt. dried, washed (pentane), soln. concd.(vac.), dissolved (pentane), crystd. at -20°C, elem. anal.;	A 100% B 98%

tri-tert-butyl phosphine (13716-12-6) → tri-tert-butylphosphine trihydroboran

Conditions	Yield
Stage #1: tri-tert-butyl phosphine With dimethylsulfide borane complex In dichloromethane at 20℃; Inert atmosphere; Stage #2: With ammonium chloride In dichloromethane; water	100%

tri-tert-butyl phosphine (13716-12-6) + [(1R)-4-((3E)-5-chloro-3-methylpent-3-en-1-ynyl)-3,5,5-trimethylcyclohex-3-en-1-yloxy]triethylsilane (1376185-70-4) → C33H62OPSi(1+)*Cl(1-)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1.5h; Wittig reaction; Inert atmosphere; stereoselective reaction;	100%

tri-tert-butyl phosphine (13716-12-6) + tris(pentafluorophenyl)borate (1109-15-5) + N-sulfinyl-4-methylaniline (15795-42-3) → C37H34BF15NOPS

Conditions	Yield
In toluene at 20℃; for 1h; Inert atmosphere;	100%

tri-tert-butyl phosphine (13716-12-6) + C31H14BBrF15NO2S → C12H27P*C31H15BBrF15NO2S(1-)*H(1+)

Conditions	Yield
With hydrogen In dichloromethane under 7500.75 Torr;	100%

tri-tert-butyl phosphine (13716-12-6) + bis[p-(methyl(2,2,2-trifluoroethyl)amino)]benzhydrylium tetrafluoroborate → C31H46F6N2P(1+)*BF4(1-)

Conditions	Yield
In dichloromethane-d2 Inert atmosphere;	100%

t-butyl bromide (507-19-7) + tri-tert-butyl phosphine (13716-12-6) + 4,8,12-trioxatriangulenium tetrakis[3,5-bis(trifluoromethyl)phenyl]-borate → C19H9BrO3 + isobutene (115-11-7) + C32H12BF24(1-)*C12H27P*H(1+)

Conditions	Yield
In acetonitrile at 20℃;	A 100% B n/a C 100%

Os3(μ-H)2(CO)10 (41766-80-7) + tri-tert-butyl phosphine (13716-12-6) → (μ-H)HOs3(CO)10(P-t-Bu3)

Conditions	Yield
In n-heptane; dichloromethane Ar-atmosphere; in CH2Cl2/heptane=1:10 v/v, excess phosphine, room temp. (UV-control); vol. reduction (Ar-stream), crystn. (-15°C);	99%

tri-tert-butyl phosphine (13716-12-6) + tris(pentafluorophenyl)borate (1109-15-5) + hydrogen (1333-74-0) → [tBu3Ph][HB(C6F5)3] (930301-81-8)

Conditions	Yield
In toluene under 1 atm of H2 at 25°C;	99%
In toluene under 3040.2 Torr; Inert atmosphere; Schlenk technique;
at 21℃; under 825.083 Torr; for 12h;
In dichloromethane-d2 at 20℃; for 1 - 12h; Sealed tube;

tris(2,3,5,6-tetrafluorophenyl)borane triethylphosphine oxide (148892-95-9) + tri-tert-butyl phosphine (13716-12-6) + hydrogen (1333-74-0) → [t-Bu3PH][HB(p-C6F4H)3] (1094249-96-3)

Conditions	Yield
In not given	99%
In hexane High Pressure; (N2); mixing hexane soln. of phosphine deriv. and borane deriv. in C6H5Br, freezing at -196°C, exposure to H2, warming to room temp., stirring overnight; pressure of H2 after warming to room temp. was 4 atm; evapn., recrystn. by addn. of hexanes to concd. CH2Cl2 soln. and keepingat -35°C for wk, elem. anal.;	87%

tri-tert-butyl phosphine (13716-12-6) → 4-(9-phenyl-9H-fluorene-9-yl)diphenylamine (851343-53-8)

Conditions	Yield
With aniline; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In 9-(4-bromophenyl)-9-phenyl-9H-fluorene; hexane; toluene	99%
With aniline; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In 9-(4-bromophenyl)-9-phenyl-9H-fluorene; hexane; toluene	99%

9-(4-bromophenyl)-9-phenyl-9H-fluorene + tri-tert-butyl phosphine (13716-12-6) → 4-(9-phenyl-9H-fluorene-9-yl)diphenylamine (851343-53-8)

Conditions	Yield
With aniline; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene	99%
With aniline; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene	99%

tri-tert-butyl phosphine (13716-12-6) + tris(pentafluorophenyl)borate (1109-15-5) + hydrogen (1333-74-0) + [13C]Carbon monoxide (1641-69-6) → C36(13)CHB2F30O(1-)*C12H27P*H(1+)

Conditions	Yield
In (2)H8-toluene at -196 - 20℃; under 3040.2 Torr; Glovebox;	99%

(tetrahydrothiophene)gold(I) chloride (39929-21-0) + tri-tert-butyl phosphine (13716-12-6) → (tri-tert-butylphosphane)gold(I) chloride (69550-28-3)

Conditions	Yield
In dichloromethane for 1.75h;	99%
In dichloromethane at 20℃; for 18h;
In tetrahydrofuran for 0.5h; Inert atmosphere; Schlenk technique;

tri-tert-butyl phosphine (13716-12-6) + C38H11B2F20N3 (1621106-54-4) → C38H10B2F20N3(1-)*C12H27P*H(1+) (1621106-62-4)

Conditions	Yield
In benzene for 0.166667h; Inert atmosphere;	99%

tri-tert-butyl phosphine (13716-12-6) + 2,6-dimethylaniline (87-62-7) → N-(2,6-dimethylphenyl)-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]amine

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0) In hexane; toluene	99%

tri-tert-butyl phosphine (13716-12-6) + boron trifluoride diethyl etherate (109-63-7) + C26H28F8Ni2O4 → C21H33BF7NiOP

Conditions	Yield
In hexane at 20℃; for 6h; Inert atmosphere;	99%

tri-tert-butyl phosphine (13716-12-6) → tris(tert-butyl)phosphine sulfide (7441-04-5)

Conditions	Yield
With pyridine dithiomonomethaphosphoryl chloride In benzene room t.;	98%
With sulfur In benzene
With triethylsilane; [Rh(H)(PEt3)3]; sulphur hexafluoride In (2)H8-toluene at 80℃; under 760.051 Torr; for 16h; Catalytic behavior; Time; Inert atmosphere;	2.9 %Spectr.

tri-tert-butyl phosphine (13716-12-6) + methyl iodide (74-88-4) → Methyl-tri-tert.-butyl-phosphoniumjodid (13954-07-9)

Conditions	Yield
In ethyl acetate at 20℃; for 24h; Inert atmosphere; Cooling with ice;	98%
In diethyl ether

tri-tert-butyl phosphine (13716-12-6) + [(t-Bu)3P](o-tolyl)PdBr → 2-methylphenyl bromide (95-46-5)

Conditions	Yield
In benzene-d6 at 70℃; Equilibrium constant;	98%

bromobenzene (108-86-1) + tri-tert-butyl phosphine (13716-12-6) → N-phenylacridan

Conditions	Yield
palladium diacetate In dichloromethane; toluene	98%
palladium diacetate In dichloromethane; toluene	98%

tri-tert-butyl phosphine (13716-12-6) → tri-t-butylphosphane hydrobromide (1021528-17-5)

Conditions	Yield
With hydrogen bromide In water at 0 - 20℃; Inert atmosphere;	98%

tri-tert-butyl phosphine (13716-12-6) + 1-amino-3-methylbenzene (108-44-1) → 3-methylphenyl-3-[9-(3-methylphenyl)-9H-fluoren-9-yl]phenylamine (1292285-24-5)

Conditions	Yield
With sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; 9-(3-bromophenyl)-9-(3-methylphenyl)fluorene; toluene	98%

tri-tert-butyl phosphine (13716-12-6) + C24H10BF15 (1391020-24-8) + hydrogen (1333-74-0) → C12H27P*C24H11BF15(1-)*H(1+) (1391020-46-4)

Conditions	Yield
at 80℃; under 3000.3 Torr; for 16h; Schlenk technique;	98%

tri-tert-butyl phosphine (13716-12-6) + (2-nitroethenyl)benzene (102-96-5) + C18H9BF6*C4H8O → C38H43BF6NOP

Conditions	Yield
In benzene for 12h; Inert atmosphere; Schlenk technique; Glovebox;	98%

1-bromo-3-(4-dibenzofuranyl)benzene (887944-90-3) + tri-tert-butyl phosphine (13716-12-6) + 2,6-dimethylaniline (87-62-7) → N-[3-(dibenzofuran-4-yl)phenyl]-N-(2,6-dimethylphenyl)amine

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0) In hexane; water; toluene	98%

tri-tert-butyl phosphine (13716-12-6) + C18H3F12N3P(1+)*C24BF20(1-) → C12H27N3P(1+)*C24BF20(1-)

Conditions	Yield
In dichloromethane	98%

Upstream product

• 677-22-5 tert-butylmagnesium chloride 
• 13716-10-4 di(tert-butyl)chlorophosphine 
• 594-19-4 tert.-butyl lithium 
• 60483-74-1 Tri-tert-butylphosphantellurid 
• 39760-34-4 tertiary butyl arsine 
• 93646-62-9 2,2',3,3'-Tetra-tert-butyl-1,1'-bicyclotriphosphan 
• 6002-40-0 methyldi-t-butylphosphine 
• 2622-14-2 tricyclohexylphosphine 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 615-37-2 ortho-methylphenyl iodide 
• 95-49-8 2-methylchlorobenzene 
• 95-46-5 2-methylphenyl bromide 
• 7441-04-5 tris(tert-butyl)phosphine sulfide 

Downstream Products

• 2622-14-2 tricyclohexylphosphine 
• 6002-40-0 methyldi-t-butylphosphine 
• 95-46-5 2-methylphenyl bromide 
• 95-49-8 2-methylchlorobenzene 
• 615-37-2 ortho-methylphenyl iodide 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 131274-22-1 tri tert-butylphosphoniumtetrafluoroborate 
• 930301-81-8 [tBu₃Ph][HB(C₆F₅)3] 
• 167218-30-6 N-(4'-anilino[1,1'-biphenyl]-4-yl)-N,N-diphenylamine 
• 19606-98-5 N,N,N'-triphenyl-p-phenylenediamine 
• 352359-41-2 N-(1-Naphthyl)-N,N'-diphenylbenzidine 
• 923020-73-9 2-(N-1-naphthyl-N-phenylamino)-7-(N-phenylamino)phenanthrene 
• 25032-49-9 di-tert-butylisopropylphosphine 

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The synthesis of an unusual T-shaped alkylpalladium(II) complex featuring a cyclometalated tri-tert-butylphosphineoxide ligand by oxidation of the corresponding cyclometalated tri-tert-butylphosphine complex with PhIO is reported. We speculate that this reaction proceeds by formation of a transient palladium oxo intermediate and there are structural similarities with a late transition metal exemplar: Milstein's seminal pincer ligated Pt(IV) oxo (Nature 2008, 455, 1093–1096).

Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we describe a simple photochemical route toward such products. UV-LED irradiation (365 nm) of chlorobenzenes, white phosphorus (P4) and the organic superphotoreductant tetrakis(dimethylamino)ethylene (TDAE) affords the desired arylphosphorus compounds in a single reaction step.

Process for synthesizing tri-tert-butylphosphonium tetrafluoroborate

A tert-butyl Grignard reagent is reacted with phosphorus trihalide and boron trifluoride, the reaction is finished, a hydrofluoric acid aqueous solution is added to form a salt, the layering is extracted, and the tri-tert-butylphosphonium - tetrafluoroborate is obtained through recrystallization. The method is simple, feasible, safe and environment-friendly. When the tert-butyl Grignard reagent is reacted with the phosphorus trihalide, the tert-butyl phosphorus intermediate acts in the reaction process by adding the boron trifluoride complex, thereby improving the halogen ion release property, improving the tri-substituted product to 94 - 95%, the reaction yield 85 - 87% and the organic solvent can be recycled.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Method for synthesizing tri-tert-butyl phosphine

The invention discloses a method for synthesizing tri-tert-butyl phosphine, belonging to the field of organic synthesis. Tri-tert-butyl phosphine is synthesized from tert-butyl bromide and calcium phosphide in anhydrous and anaerobic atmosphere under the catalyst action of a nickel catalyst. Compared with the prior art, the invention has the advantages of mild reaction conditions, simple operation, high yield, simple and easy-to-obtain raw materials, reduced production cost and being suitable for industrial production.

Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs

The present invention relates to phosphorescent organic light-emitting diodes (OLEDs) comprising a hole-transporting or a hole-transporting and an electron-blocking layer comprising an N,N,N',N'-tetraaryl-phenylene-3,5-diamine or an N,N,N',N'-tetraaryl-1,1'-biphenyl-3,3'-diamine matrix compound and to new N,N,N',N'-tetraarylsubstituted m-arylene diamine compounds useful as hole-transporting and electron-blocking layer matrices in phosphorescent OLEDs.

Reactivity and Moessbauer spectroscopic characterization of an Fe(IV) ketimide complex and reinvestigation of an Fe(IV) norbornyl complex

Thermolysis of Fe(Ni=CtBu2)4 (1) for 8 h at 50 °C generates the mixed valent Fe(III)/Fe(II) bimetallic complex Fe2(Ni=CtBu2)5 (2) in moderate yield. Also formed in this reaction

Bis-boranes in the frustrated Lewis pair activation of carbon dioxide

Using a frustrated Lewis pair approach, the 1,1-bis-(C6F 5)2BOB(C6F5)2 is shown to bind CO2 in a monodentate fashion, while the bis-boranes (X 2B)2CCMe2 (X = Cl, C6F5) give bidentate chelation of CO2 affording unique heterocycles.