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
• Article Data: 22

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

Reaction

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

Chemical Properties

Colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 13716-12-6 differently. You can refer to the following data:
1. Tri-tert-butylphosphine is used primarily in the preparation of mono- and bidentate phosphine ligands in metal complexes for catalytic chiral asymmetric hydrogenations and other asymmetric reactions as well as transition metal coupling reactions. This reagent is also used in the preparation of other phosphines in catalytic polymerization reactions.
2. Valuable ligand for several coupling reactions. This product is offered as the THF solution for more convenient handling.

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

• 60483-74-1 Tri-tert-butylphosphantellurid 
• 39760-34-4 tertiary butyl arsine 
• 2622-14-2 tricyclohexylphosphine 
• 507-20-0 tertiary butyl chloride 
• 60648-70-6 bis(tri-tert-butylphosphine)platinum⁽⁰⁾ 
• 849926-75-6 bis(pentamethylcyclopentadienyl)dizinc 
• 507-19-7 t-butyl bromide 
• 7441-04-5 tris(tert-butyl)phosphine sulfide 
• 594-19-4 tert.-butyl lithium 
• 13716-10-4 di(tert-butyl)chlorophosphine 
• 677-22-5 tert-butylmagnesium chloride 
• 7719-12-2 phosphorus trichloride 
• 95-46-5 2-methylphenyl bromide 
• 95-49-8 2-methylchlorobenzene 

Downstream Products

• 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 
• 537705-08-1 CP-724714 
• 479080-93-8 1-triisopropylsilanyl-4-(4-benzyl-piperazin-1-yl)-1H-indole 
• 366015-87-4 N-phenyl-3-methoxyacridan 
• 90-41-5 2-phenylaniline 
• 92-54-6 4-phenyl-1-piperazine 
• 31144-33-9 N,N-dibutyl-4-methylaniline 
• 82749-64-2 N,N-dibutyl-2-methylaniline 
• 167283-32-1 N-(p-tolyl)indole 
• 14618-59-8 N-(tert-butoxycarbonyl)-4-methylaniline 

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A PdP(t-Bu)3 catalyst system has revealed very high activity and selectivity for the amination of N-(hetero)aryl halides with unprotected piperazine. A wide variety of N-(hetero)arylpiperazines could be prepared using this catalyst. Turnover numbers up to 6400mol/mol have been obtained.detailed

Synthesis, structures and spectroscopic properties of cyclometalated Tri-tert-butylphosphine (cas 13716-12-6) complexes of platinum(II)09/08/2019

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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.