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603-35-0 Usage

description

Triphenylphosphine (TPP) is an important ligand, and is also utilized in the Wittig reaction for alkene synthesis. This reaction involves the formation of alkyliden-etriphenylphosphoranes from the action of butyllithium or other base on the quarternary halide.Triphenylphosphine is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. TPP is a highly efficient product that serves successfully in many applications, for example:The important ligands of homogeneous catalysts used in petrochemicals and fine chemicals production, as a co-catalyst in isobutanol and n-butanol production.The basic raw material of rhodium phosphine complex catalyst, It is used to prepare Wilkinson's catalyst, RhCl(PPh3)3 useful to catalyze the hydrogenation of alkenes and tetrakis(triphenylphosphine)palladium(0) that is widely used to catalyze C-C coupling reactions in organic synthesis.In the dye industry, Triphenylphosphine is used as sensitizer, heat stabilizers, light stabilizers, antioxidants, flame retardants, antistatic agents, rubber antiozonants and analytical reagent.

Chemical properties

Triphenylphosphine is a common organophosphorus compound with the formula P(C6H5)3 - often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless to pale yellow monoclinic crystals at room temperature. It is a colorless to pale yellow transparent oily liquid above the room temperature with skin irritation and a pungent odour. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

Name Reactions

Mitsunobu reactions The triphenylphosphine combines with DEAD to generate a phosphonium intermediate that binds to the alcohol oxygen, activating it as a leaving group. Substitution by the carboxylate, mercaptyl, or other nucleophile completes the process. Ozonolysis reactions Ozonolysis allows the cleavage of alkene double bonds by reaction with ozone. Depending on the work up, different products may be isolated: reductive work-up gives either alcohols or carbonyl compounds, while oxidative work-up leads to carboxylic acids or ketones. Staudinger reactions Triphenylphosphine reacts with the azide to generate a phosphazide, which loses N2 to form an iminophosphorane. Aqueous work up leads to the amine and the very stable phosphine oxide. Appel reactions The reaction of triphenylphosphine and tetrahalomethanes (CCl4, CBr4) with alcohols is a ready method to convert an alcohol to the corresponding alkyl halide under mild conditions. The yields are normally high. This reaction is somewhat similar to the Mitsunobu Reaction, where the combination of a phosphine, a diazo compound as a coupling reagent, and a nucleophile are used to invert the stereochemistry of an alcohol or displace it.

Uses

Different sources of media describe the Uses of 603-35-0 differently. You can refer to the following data:
1. Triphenylphosphine is first sulfonated with oleum to form the trisulfonic acid.Triphenylphosphine can be used in Wittig synthesis. It is a standard ligand in homogeneous catalysis.Triphenylphosphine is used in the synthesis of an organophosphorus intermediate, trimethyl phosphite in ester exchange method. And then a series of organophosphorus pesticides such as dichlorvos, monocrotophos and phosphamidon can be further obtained.In addition, it can be used as stabilizers in the synthesis of rubber and resins, antioxidants in polyvinyl chloride, and raw material in the synthesis of alkyd resins and polyester resins.
2. Triphenylphosphine is used in the synthesis of Chlorambucil with cytotoxicity in breast and pancreatic cancers. Also used in the preparation of α-Tocopherol analogues for monitoring antioxidant status.

Production methods

In this preparation method, phenol and phosphorus trichloride was used as raw materials. After esterification and vacuum distillation, the product namely triphenyl phosphite can be obtained. 3C6H5OH + PCl3 [15~20 ℃] → (C3H5O) 3P + 3HCl Specific process can be classified into batch and continuous processes. ?(1) Batch process The phenol was added into the reactor, after warming to melt phosphorus trichloride was added to react with phenol at 70~90 ℃. After the phosphorus trichloride addition was completed, the temperature of reaction mixture was raised to about 150 ℃. After the removal of hydrogen chloride and unreacted phenol dissolved under reduced pressure at a high temperature, the product can be achieved. (2) The use of a tower reactor Phenol was feeding under the condenser located in the upper portion of the tower, while phosphorus trichloride enters above the receptacle located in the lower portion of the tower. Both reacted in the tower, and the product was collected in the receiver, meanwhile by-product hydrogen chloride was introduced into the absorber tower via the upper end of the condenser. After some process of the crude ester such as distillation, the product can be obtained.

Chemical Properties

Triphenylphosphine is a white to light tan flaked solid. Insoluble inwater; slightly soluble in alcohol; soluble in benzene, acetone, carbon tetrachloride. Combustible.

Production Methods

Triphenylphosphine is one of the most widely used phosphorus-containing reagents in organic synthesis for many types of transformations such as the Mitsunobu, the Wittig, and the Staudinger reaction. Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium. PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl

Definition

ChEBI: Triphenylphosphine is a member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups. It has a role as a reducing agent. It is a member of benzenes and a tertiary phosphine.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 625, 1994 DOI: 10.1016/S0040-4039(00)75855-2

General Description

Rhodium and triphenylphosphine catalyst system has been used for the hydroformylation of soybean, safflower and linseed oils and their methyl esters. Polymer supported triphenylphosphine has been reported to efficiently catalyze the γ-addition of pronucleophiles to alkynoate. Triphenylphosphine reacts with hydrated ruthenium trichloride in methanol to afford [RuCl2(PPh3)4], [RuCl2(PPh3)3] and [RuCl3(PPh3)2CH3OH]. It participates in the Heck reaction of 4-bromoanisole and ethyl acrylate in ionic liquids.

Reactivity Profile

Triphenylphosphine reacts vigorously with oxidizing materials. .

Health Hazard

ACUTE/CHRONIC HAZARDS: Toxic; when heated to decomposition, emits highly toxic fumes of phosphine and POx.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. A skin and eye irritant. Combustible when exposed to heat or flame. Slight explosion hazard in the form of vapor when exposed to flame. Can react vigorously with oxidizing materials. To fight fire, use dry chemical, fog, CO2. When heated to decomposition it emits highly toxic fumes of phosphne and POx. See also PHOSPHINE and PHENOL.

Purification Methods

It crystallises from hexane, MeOH, diethyl ether, CH2Cl2/hexane or 95% EtOH. Dry it at 65o/<1mm over CaSO4 or P2O5. Chromatograph it through alumina using (4:1) *benzene/CHCl3 as eluent. [Blau & Espenson et al. J Am Chem Soc 108 1962 1986, Buchanan et al. J Am Chem Soc 108 1537 1986, Randolph & Wrighton J Am Chem Soc 108 3366 1986, Asali et al. J Am Chem Soc 109 5386 1987.] It has also been crystallised twice from pet ether and 5 times from Et2O/EtOH to give m 80.5o. Alternatively, dissolve it in conc HCl, and upon dilution with H2O it separates because it is weakly basic, it is then crystallised from EtOH/Et2O. It recrystallises unchanged from AcOH. [Forward et al. J Chem Soc Suppl. p121 1949, Muller et al. J Am Chem Soc 78 3557 1956.] 3Ph3P.4HCl crystallises out when HCl gas is bubbled through an Et2O solution, it has m 70-73o, but recrystallises very slowly and is deliquescent. The hydriodide, made by adding Ph3P to hydriodic acid, is not hygroscopic and decomposes at ~100o. The chlorate (1:1) salt has m 165-167o, but decomposes slowly at 100o. All salts hydrolyse in H2O to give Ph3P [IR, UV: Sheldon & Tyree J Am Chem Soc 80 2117 1958, pK: Henderson & Streuli J Am Chem Soc 82 5791 1960, Kosolapoff, Organophosphorus Compounds, Wiley 1950]. [Beilstein 16 IV 951.] § Available commercially on a polystyrene or polyethyleneglycol support.

Check Digit Verification of cas no

The CAS Registry Mumber 603-35-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 3 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 603-35:
(5*6)+(4*0)+(3*3)+(2*3)+(1*5)=50
50 % 10 = 0
So 603-35-0 is a valid CAS Registry Number.
InChI:InChI=1/C18H15P.BrH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H

603-35-0 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (T0519)  Triphenylphosphine  >95.0%(T)

  • 603-35-0

  • 25g

  • 97.00CNY

  • Detail
  • TCI America

  • (T0519)  Triphenylphosphine  >95.0%(T)

  • 603-35-0

  • 100g

  • 240.00CNY

  • Detail
  • TCI America

  • (T0519)  Triphenylphosphine  >95.0%(T)

  • 603-35-0

  • 500g

  • 380.00CNY

  • Detail
  • Alfa Aesar

  • (A14089)  Triphenylphosphine, flake, 99%   

  • 603-35-0

  • 250g

  • 679.0CNY

  • Detail
  • Alfa Aesar

  • (A14089)  Triphenylphosphine, flake, 99%   

  • 603-35-0

  • 1000g

  • 2088.0CNY

  • Detail
  • Alfa Aesar

  • (A14089)  Triphenylphosphine, flake, 99%   

  • 603-35-0

  • 5000g

  • 4974.0CNY

  • Detail
  • Alfa Aesar

  • (L02502)  Triphenylphosphine, powder, 99%   

  • 603-35-0

  • 50g

  • 303.0CNY

  • Detail
  • Alfa Aesar

  • (L02502)  Triphenylphosphine, powder, 99%   

  • 603-35-0

  • 250g

  • 728.0CNY

  • Detail
  • Alfa Aesar

  • (L02502)  Triphenylphosphine, powder, 99%   

  • 603-35-0

  • 1000g

  • 2524.0CNY

  • Detail
  • Alfa Aesar

  • (14112)  Triphenylphosphine, 99+%   

  • 603-35-0

  • 25g

  • 180.0CNY

  • Detail
  • Alfa Aesar

  • (14112)  Triphenylphosphine, 99+%   

  • 603-35-0

  • 100g

  • 401.0CNY

  • Detail
  • Alfa Aesar

  • (14112)  Triphenylphosphine, 99+%   

  • 603-35-0

  • 500g

  • 1325.0CNY

  • Detail

603-35-0SDS

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 Triphenylphosphine

1.2 Other means of identification

Product number -
Other names PP-360

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:603-35-0 SDS

603-35-0Synthetic route

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 5h;100%
With aluminium hydride*tetrahydrofuran100%
With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In methyl cyclohexane at 80℃; for 14h;100%
methanol
67-56-1

methanol

dibromure de vinylene-1,2 bis-triphenylphosphonium

dibromure de vinylene-1,2 bis-triphenylphosphonium

A

bromure de methoxyvinyltriphenylphosphonium
56351-16-7

bromure de methoxyvinyltriphenylphosphonium

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With potassium cyanide In dimethyl sulfoxide for 22h; Ambient temperature;A 86%
B 100%
dibromure de vinylene-1,2 bis-triphenylphosphonium

dibromure de vinylene-1,2 bis-triphenylphosphonium

A

bromure de methoxyvinyltriphenylphosphonium
56351-16-7

bromure de methoxyvinyltriphenylphosphonium

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With potassium cyanide In dimethyl sulfoxide for 22h; Ambient temperature;A 86%
B 100%
triphenylphosphinediiodogermylene
97939-92-9

triphenylphosphinediiodogermylene

phenyllithium
591-51-5

phenyllithium

A

iodobenzene
591-50-4

iodobenzene

B

biphenyl
92-52-4

biphenyl

C

triphenylgermane
2816-43-5

triphenylgermane

D

tetraphenylgermane
1048-05-1

tetraphenylgermane

E

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:4 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 10%
B 13%
C 39%
D 36%
E 100%
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:1 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 2.9%
B 2.9%
C 1.9%
D 14%
E 82%
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:2 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 7.7%
B 9.6%
C 1.3%
D 19%
E 79%
methanol
67-56-1

methanol

triphenylphosphine borane
2049-55-0

triphenylphosphine borane

A

Trimethyl borate
121-43-7

Trimethyl borate

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
at 120℃; Inert atmosphere; Microwave irradiation;A n/a
B 99%
benzonitrile
100-47-0

benzonitrile

(trimethylsilyl)diphenylphosphine
17154-34-6

(trimethylsilyl)diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With cis-[NiCl2(PPh3)2]; potassium tert-butylate In 1,4-dioxane at 90℃; for 10h; Inert atmosphere;99%
fluorobenzene
462-06-6

fluorobenzene

sodium diphenylphosphide
4376-01-6

sodium diphenylphosphide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 15-crown-5 In tetrahydrofuran at 25℃; for 16h; Reagent/catalyst; Inert atmosphere;99%
dichlorotriphenylphosphorane
2526-64-9

dichlorotriphenylphosphorane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With tributylphosphine98%
With sodium
With bis(2-methylphenyl)disulfide; triethylamine In chloroform for 7h; Heating;
2-[2-Oxo-1-(triphenyl-λ5-phosphanylidene)-propyl]-1,2-dihydro-indazol-3-one
103748-75-0

2-[2-Oxo-1-(triphenyl-λ5-phosphanylidene)-propyl]-1,2-dihydro-indazol-3-one

A

2-acetyl-4-oxo-dihydroquinazoline
17244-28-9

2-acetyl-4-oxo-dihydroquinazoline

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In toluene at 95℃; for 2h;A 98%
B n/a
iodobenzene
591-50-4

iodobenzene

diphenylphosphane
829-85-6

diphenylphosphane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With potassium acetate; 5percent Pd on charcoal In N,N-dimethyl-formamide at 190℃; for 0.05h; microwave irradiation;98%
With caesium carbonate In toluene at 115℃; for 24h; Inert atmosphere;90%
With potassium acetate In N,N-dimethyl acetamide at 130℃; for 3h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;86%
With rongalite; potassium hydroxide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;65%
chlorobenzene
108-90-7

chlorobenzene

potassium diphenylphosphine
15475-27-1, 4346-39-8

potassium diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 25 - 67℃; for 74.4h;98%
phenyl sodium
1623-99-0

phenyl sodium

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With phosphorus tribromide97.3%
With anhydrous phosphorus trichloride In toluene
cis-dichlorobis(triphenylphosphine)platinum(II)
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

cyclenphosphorane
64317-97-1

cyclenphosphorane

cis-((H2cyclen)P)PtCl2PPh3}Cl
108148-25-0

cis-((H2cyclen)P)PtCl2PPh3}Cl

{(eta.2-cyclenphosphorane)PtClPPh3}
108148-24-9

{(eta.2-cyclenphosphorane)PtClPPh3}

C

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In tetrahydrofuran under N2, mixt. of phosphorane and Pt complex in THF was stirred for 12h, pptn.; volatiles removed in vac., residue washed (10 times hexane, 10 times THF (to dissolve the η2-complex), residue (cis complex) and washing (η2.-complex) pumped dry separately, each heated to 90°C under vac., elem. anal.;A 96%
B 97%
C 97%
chlorobenzene
108-90-7

chlorobenzene

sodium diphenylphosphide
4376-01-6

sodium diphenylphosphide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 15-crown-5 In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; for 3h; Reagent/catalyst; Inert atmosphere;97%
Diphenylphosphonigsaeure-trimethylsilylester
13683-01-7

Diphenylphosphonigsaeure-trimethylsilylester

phenyllithium
591-51-5

phenyllithium

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;97%
benzylpotassium
3605-36-5

benzylpotassium

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
96.6%
triphenylphosphine sulfide
3878-45-3

triphenylphosphine sulfide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 80℃; for 1h; Product distribution; Further Variations:; Reaction partners; reaction times;96%
With n In tetrahydrofuran at 60℃; for 3h;95%
Stage #1: triphenylphosphine sulfide With oxalyl dichloride In toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran; toluene at 20℃; for 0.5h; Inert atmosphere;
88%
2-methyl-2-(triphenylphosphonio)dithiopropionate betaine
69491-12-9

2-methyl-2-(triphenylphosphonio)dithiopropionate betaine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

2-isopropylidene-4,5-dimethoxycarbonyl-1,3-dithiole
85072-91-9

2-isopropylidene-4,5-dimethoxycarbonyl-1,3-dithiole

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In acetonitrile for 24h; Ambient temperature;A 96%
B 67%
Triphenylphosphine selenide
3878-44-2

Triphenylphosphine selenide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 80℃; for 2h;96%
{Fe(C5H4S)2}Pt(P(C6H5)3)2

{Fe(C5H4S)2}Pt(P(C6H5)3)2

{Fe(C5H4S)2}Pt(P(C6H5)3)*C6H6

{Fe(C5H4S)2}Pt(P(C6H5)3)*C6H6

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In chloroform soln. of educt in CHCl3 heated to 60°C and stirred for 0.5 h under N2, cooled; concd. in vac., chromd. (SiO2, C6H6), 1st colorless fraction contained PPh3, red 2nd fraction collected, concd.;A 96%
B n/a
sodium methylate
124-41-4

sodium methylate

dibromure de vinylene-1,2 bis-triphenylphosphonium

dibromure de vinylene-1,2 bis-triphenylphosphonium

A

triphenylphosphine
603-35-0

triphenylphosphine

B

2-triphenylphosphoniumacetaldehyde dimethyl acetal bromide

2-triphenylphosphoniumacetaldehyde dimethyl acetal bromide

Conditions
ConditionsYield
In methanol for 0.75h; Ambient temperature;A 95%
B 89%
ethanol
64-17-5

ethanol

triphenylphosphine borane
2049-55-0

triphenylphosphine borane

A

triethyl borate
150-46-9

triethyl borate

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 95%
triphenylphosphine borane
2049-55-0

triphenylphosphine borane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 96h; Inert atmosphere; Molecular sieve; Reflux;95%
With diisopropylamine In toluene at 30℃; Kinetics; Equilibrium constant; Reagent/catalyst; Solvent;
S-(4-linoleyloxybutyl)thioacetate

S-(4-linoleyloxybutyl)thioacetate

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 4.5h; Inert atmosphere; Cooling with ice;95%
3,3,4,4-tetramethyl-1,2-dioxetane
35856-82-7

3,3,4,4-tetramethyl-1,2-dioxetane

2,2-Dihydro-4,4,5,5-tetramethyl-2,2,2-triphenyl-1,3,2-dioxaphospholane
49595-63-3

2,2-Dihydro-4,4,5,5-tetramethyl-2,2,2-triphenyl-1,3,2-dioxaphospholane

A

3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In benzene-d6 at 23.9℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, Ea, ΔS(excit);A 6%
B 94%
iodobenzene
591-50-4

iodobenzene

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide; palladium dichloride at 120℃; for 0.5h; Inert atmosphere;93%
With nickel tetrafluoroborate; lithium chloride In acetonitrile electrolysis; var. supporting electrolytes, other aryl and alkyl halides;80%
With pyridine; tris-(trimethylsilyl)silane; 1,1'-azobis(1-cyanocyclohexanenitrile) In benzene for 20h; Heating;
2-{[(Toluene-4-sulfonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-azo}-benzaldehyde
103748-72-7

2-{[(Toluene-4-sulfonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-azo}-benzaldehyde

A

2-p.tosyl-4-oxo-dihydroquinazoline
103748-77-2

2-p.tosyl-4-oxo-dihydroquinazoline

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In toluene at 70℃; for 5h;A 93%
B n/a
chlorobenzene
108-90-7

chlorobenzene

(trimethylsilyl)diphenylphosphine
17154-34-6

(trimethylsilyl)diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; potassium tert-butylate In 1,4-dioxane at 90℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere;93%
1-(benzoyl)piperidine-2,6-dione

1-(benzoyl)piperidine-2,6-dione

diphenylphosphane
829-85-6

diphenylphosphane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); sodium carbonate In 1,4-dioxane at 160℃; for 48h; Reagent/catalyst; Inert atmosphere; Schlenk technique;93%
1,3-propanesultone
1120-71-4

1,3-propanesultone

triphenylphosphine
603-35-0

triphenylphosphine

3-(triphenylphosphonio)propane-1-sulfonate
116154-22-4

3-(triphenylphosphonio)propane-1-sulfonate

Conditions
ConditionsYield
In toluene for 12h; Reflux;100%
In tetrahydrofuran at 25℃;95%
In toluene for 24h; Reflux;43%
benzyl bromide
100-39-0

benzyl bromide

triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium bromide
1449-46-3

benzyltriphenylphosphonium bromide

Conditions
ConditionsYield
In xylene for 0.00833333h; Heating; microwave irradiation;100%
In toluene for 12h; Reflux;100%
at 100℃; for 0.0333333h; Irradiation;99%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

triphenylphosphine
603-35-0

triphenylphosphine

(methoxymethyl)triphenylphosphonium chloride
4009-98-7

(methoxymethyl)triphenylphosphonium chloride

Conditions
ConditionsYield
In dichloromethane Reflux;100%
In toluene at 95℃; for 16h;97.3%
In neat (no solvent) at 80℃; for 4h; Solvent; Temperature; Time; Inert atmosphere; Schlenk technique;93%
1-dodecylbromide
143-15-7

1-dodecylbromide

triphenylphosphine
603-35-0

triphenylphosphine

dodecyltriphenylphosphonium bromide
15510-55-1

dodecyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene Reflux;100%
In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 48h;96.1%
In tetrahydrofuran for 12h; sealed tube, bath temperature 250 deg C;88%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

triphenylphosphine
603-35-0

triphenylphosphine

(methyloxycarbonylmethyl)triphenylphosphonium bromide
1779-58-4

(methyloxycarbonylmethyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 17h;100%
In ethyl acetate97%
In benzene at 20℃; for 4h;97%
α-bromoacetophenone
70-11-1

α-bromoacetophenone

triphenylphosphine
603-35-0

triphenylphosphine

triphenylphenacylphosphonium bromide
6048-29-9

triphenylphenacylphosphonium bromide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;100%
at 20℃; for 24h;100%
In toluene for 4h; Reflux;99%
p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

triphenylphosphine
603-35-0

triphenylphosphine

4-methoxy-N-(triphenylphosphoran-ylidene)-aniline
14796-89-5

4-methoxy-N-(triphenylphosphoran-ylidene)-aniline

Conditions
ConditionsYield
In toluene at 60℃; for 16h; Schlenk technique; Inert atmosphere;100%
In diethyl ether at 20℃; for 2h;88%
triphenylphosphine
603-35-0

triphenylphosphine

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

3-bromopropyltriphenylphosphonium bromide
3607-17-8

3-bromopropyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene at 110℃; for 16h;100%
In toluene for 24h; Reflux;99%
In toluene Inert atmosphere; Reflux;98%
triphenylphosphine
603-35-0

triphenylphosphine

Phenyl azide
622-37-7

Phenyl azide

N-phenyltriphenyliminophosphorane
2325-27-1

N-phenyltriphenyliminophosphorane

Conditions
ConditionsYield
In toluene at 20℃; for 2h; Condensation;100%
In diethyl ether for 2h; Heating;100%
In diethyl ether at 20℃; for 2h;79%
triphenylphosphine
603-35-0

triphenylphosphine

hexadecanyl bromide
112-82-3

hexadecanyl bromide

(1-hexadecyl)triphenylphosphonium bromide
14866-43-4

(1-hexadecyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene Reflux;100%
In toluene at 90℃; for 48h;79%
In acetonitrile for 36h; Heating;68%
triphenylphosphine
603-35-0

triphenylphosphine

diazodiphenylmethane
908093-98-1

diazodiphenylmethane

diphenyldiazomethane triphenylphosphazine
1109-01-9

diphenyldiazomethane triphenylphosphazine

Conditions
ConditionsYield
In benzene at 30℃; for 0.00333333h;100%
In acetonitrile at 30℃; Rate constant;
In acetonitrile at 30℃; Kinetics; Thermodynamic data; effect of 4,4'-disubstitution on the reactivity;
triphenylphosphine
603-35-0

triphenylphosphine

methyl iodide
74-88-4

methyl iodide

methyl-triphenylphosphonium iodide
2065-66-9

methyl-triphenylphosphonium iodide

Conditions
ConditionsYield
for 0.00833333h; Heating; microwave irradiation;100%
In toluene at 0℃; for 4h; Reflux;100%
In dichloromethane at 20℃; Inert atmosphere;100%
triphenylphosphine
603-35-0

triphenylphosphine

9-diazofluorenone
832-80-4

9-diazofluorenone

9-fluorenone triphenylphosphazine
751-35-9

9-fluorenone triphenylphosphazine

Conditions
ConditionsYield
In benzene at 30℃; for 0.00333333h;100%
With benzene
In acetonitrile
In acetonitrile Yield given;
triphenylphosphine
603-35-0

triphenylphosphine

Triphenylphosphine selenide
3878-44-2

Triphenylphosphine selenide

Conditions
ConditionsYield
With selenium In toluene for 6h; Heating;100%
With 4-phenyl-1,2,3-selenadiazole In benzene for 1h; Heating;100%
With selenium In chloroform-d1 at 20℃;100%
triphenylphosphine
603-35-0

triphenylphosphine

triphenylphosphine diiodide
6396-07-2

triphenylphosphine diiodide

Conditions
ConditionsYield
With iodine In diethyl ether at 20℃; for 1h;100%
With iodine In diethyl ether; toluene96%
With iodine
With 1,2-Diiodoethane In acetonitrile at 60℃; for 0.5h;
With iodine In dichloromethane at 0℃; for 2h;
triphenylphosphine
603-35-0

triphenylphosphine

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
With CuO2H In acetonitrile at 70℃; for 6h;100%
With CuO2H In acetonitrile at 70℃; for 6h;100%
With periodate form of Amberlyst A26 In chloroform at 25℃; for 2h;100%
p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

triphenylphosphine
603-35-0

triphenylphosphine

((4-methoxyphenyl)methyl)triphenylphosphonium bromide
1530-38-7

((4-methoxyphenyl)methyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In benzene for 24h; Ambient temperature;100%
In toluene at 110℃;99%
In toluene for 10h; Inert atmosphere; Reflux;98%
benzyl chloride
100-44-7

benzyl chloride

triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
In toluene at 110℃; Inert atmosphere;100%
In toluene Inert atmosphere; Reflux;98%
In toluene for 18h; Inert atmosphere; Reflux;98%
4-Methylbenzyl chloride
104-82-5

4-Methylbenzyl chloride

triphenylphosphine
603-35-0

triphenylphosphine

(4-methylbenzyl)triphenylphosphonium chloride
1530-37-6

(4-methylbenzyl)triphenylphosphonium chloride

Conditions
ConditionsYield
In acetonitrile for 4.5h; Reflux;100%
In acetonitrile for 4.5h; Reflux;100%
In xylene for 18h; Heating;86%
1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

triphenylphosphine
603-35-0

triphenylphosphine

4-bromobenzyl triphenylphosphonium bromide
51044-13-4

4-bromobenzyl triphenylphosphonium bromide

Conditions
ConditionsYield
In chloroform for 4h; Heating / reflux;100%
In acetonitrile for 4.5h; Reflux;100%
In acetone at 20℃; for 12h;99%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

triphenylphosphine
603-35-0

triphenylphosphine

but-3-en-1-yltriphenylphosphonium bromide
16958-42-2

but-3-en-1-yltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 24h; Inert atmosphere; Reflux;100%
In N,N-dimethyl-formamide for 3h; Heating;84%
In acetonitrile at 23℃; for 23h; Reflux; Inert atmosphere;81%
triphenylphosphine
603-35-0

triphenylphosphine

prenyl bromide
870-63-3

prenyl bromide

(3-methylbut-2-enyl)triphenylphosphonium bromide
1530-34-3

(3-methylbut-2-enyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene at 110℃; Inert atmosphere;100%
In benzene at 20℃; for 20h;96%
In toluene Ambient temperature;93%
[14C]methyl iodide
16170-82-4

[14C]methyl iodide

triphenylphosphine
603-35-0

triphenylphosphine

-methyltriphenylphosphonium iodide
1560-52-7

-methyltriphenylphosphonium iodide

Conditions
ConditionsYield
In benzene at 22℃; for 37h;100%
In diethyl ether Methylation;95%
In benzene for 24h;90%
(E)-1-bromo-2-hexene
73881-10-4

(E)-1-bromo-2-hexene

triphenylphosphine
603-35-0

triphenylphosphine

<(E)-hex-2-enyl>triphenylphosphonium bromide
88517-93-5

<(E)-hex-2-enyl>triphenylphosphonium bromide

Conditions
ConditionsYield
In benzene for 5h; Heating;100%
1-bromo-hexane
111-25-1

1-bromo-hexane

triphenylphosphine
603-35-0

triphenylphosphine

hexyltriphenylphosphonium bromide
4762-26-9

hexyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 8h; Reflux;100%
In acetonitrile for 16h; Heating;95.6%
In toluene for 120h; Heating;92%
iodomethane-d3
865-50-9

iodomethane-d3

triphenylphosphine
603-35-0

triphenylphosphine

(methyl-d3)triphenylphosphonium iodide
1560-56-1

(methyl-d3)triphenylphosphonium iodide

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Reflux;100%
In tetrahydrofuran for 1h; Schlenk technique; Reflux;99%
In tetrahydrofuran for 1h; Schlenk technique; Inert atmosphere; Reflux;99%
1-bromo-octane
111-83-1

1-bromo-octane

triphenylphosphine
603-35-0

triphenylphosphine

n-octyltriphenylphosphoniumbromide
42036-78-2

n-octyltriphenylphosphoniumbromide

Conditions
ConditionsYield
In chlorobenzene for 48h; Heating;100%
In toluene Reflux;100%
In o-xylene Heating;98.7%
1-Bromotetradecane
112-71-0

1-Bromotetradecane

triphenylphosphine
603-35-0

triphenylphosphine

(n-tetradecyl)triphenylphosphonium bromide
25791-20-2

(n-tetradecyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene Reflux;100%
at 140℃; for 7h;92%
In benzene for 48h; Substitution; Heating;92%
6-bromohexanoic acid
4224-70-8

6-bromohexanoic acid

triphenylphosphine
603-35-0

triphenylphosphine

(5-carboxypentyl)triphenylphosphonium bromide
50889-29-7

(5-carboxypentyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In acetonitrile for 16h; Heating;100%
at 100℃; for 4h;100%
In acetonitrile for 24h; Heating;99%

603-35-0Relevant articles and documents

-

Wunsch et al.

, p. 33,35,36 (1969)

-

Synthesis and characterization of the [Ni6Ge13(CO) 5]4- and [Ge9Ni2(PPh 3)]2- Zintl ion clusters

Esenturk, Emren N.,Fettinger, James,Eichhorn, Bryan

, p. 521 - 529 (2006)

Reactions between K4Ge9, Ni(CO)2(PPh 3)2, and 2,2,2-crypt in ethylenediamine solutions give two different products depending on reaction conditions. The [Ni6Ge 13(CO)5]4- ion (1) is formed at low temperatures (~40°C) and short reaction times whereas the [Ge 9Ni2(PPh3)]2- ion (2) forms at higher temperatures (~118°C). Both complexes were isolated as [K(2,2,2-crypt)]+ salts and characterized by single-crystal X-ray diffraction, electrospray mass spectrometry (ESI-MS) and NMR studies ( 13C and 31P). 1 has a hypo-closo cluster electron count (Wades Rules) and adopts an interpenetrating biicosahedral structure with 17 vertices and 2 interstitials, which is unique in transition metal Zintl ion clusters. 2 also has a hypo-closo cluster electron count but displays an open, nido-like 10-vertex structure with a Ni interstitial. The composition of 2 was established through ESI-MS studies and corrects an earlier report that characterized the cluster as [Ge10Ni(PPh3)]2- with an interstitial Ge.

Benedikt, M.,Schloegl, K.

, (1978)

Reactions of but-2-yne-1,4-diylbis(triphenylphosphonium) dihalides with SH- and NH-nucleophiles

Bichakhchyan

, p. 1041 - 1045 (2016)

But-2-yne-1,4-diylbis(triphenylphosphonium) diiodide reacts with 2-sulfanylethan-1-ol in the presence of triethylamine to form a 1 : 1 adduct. Under similar conditions, ethane-, butane- and 2-methylbutane- 1-thiols form [4-(alkylsulfanyl)buta-1,3-dien-1-yl]triphenylphosphonium iodides, probably via β-cleavage of the original salt involving vinylethynyl intermediate. Features of the reaction of but-2-ynebisphosphonium salt with 3,5-dimethylpyrazole, hydrazine and its derivatives have been studied.

Eaton,Suart

, p. 4170 (1968)

Phosphane-functionalized heavier tetrylenes: Synthesis of silylene- And germylene-decorated phosphanes and their reactions with Group 10 metal complexes

Cabeza, Javier A.,García-álvarez, Pablo,Laglera-Gándara, Carlos J.,Pérez-Carre?o, Enrique

, p. 8331 - 8339 (2020)

The stable phosphane-functionalized heavier tetrylenes E(tBu2bzam)pyrmPtBu2 (E = Si (1Si), Ge (1Ge); tBu2bzam = N,N′-ditertbutylbenzamidinate; HpyrmPtBu2 = ditertbutyl(2-pyrrolylmethyl)phosphane) have been prepared by reacting the amidinatotetrylenes E(tB

Synthesis and structural characterization of isomeric 'lantern-shaped' platinum(III) complexes of formula [Pt2(PPh3)X{N(H)C(R)O}4](NO3) 2 (X=PPh3, H2O)

Bandoli, Giuliano,Dolmella, Alessandro,Intini, Francesco P.,Pacifico, Concetta,Natile, Giovanni

, p. 143 - 150 (2003)

The platinum(III) lantern type complexes [Pt2(PPh3)2{N(H)C(R)O}4](NO 3)2 [R=Me (1), But (2)], and [Pt2(H2O)(PPh3){N(H)C(But)O} 4](NO3)2 (3) were synthesized and characterized by 1H NMR and X-ray crystallography (2 and 3). The compounds can give rise to formation of isomers differing for the sets of equatorial donor atoms around each platinum, N3O/NO3 or N2O2, and, in the case of N2O2, for the cis or trans geometry. The effect of the anion upon the chemical shifts of NH protons was studied for NO3-, BF4-, and ClO4-. The stability of phosphine axial ligands in the complexes N3O/NO3-[Pt2(PPh3) 2{N(H)C(R)O}4](NO3)2 as a function of the set of donor atoms was also studied. The complex N3O/NO3-3 is the fist non-symmetric lantern-type platinum dimer to be characterized by X-ray diffraction. Comparison of the platinum/axial ligand bond distances in different complexes of this type allows to conclude that two factors contribute to the lengthening of axial bonds: the strong trans labilizing effect of the intermetallic bond and the trans-influence of the axial ligand on the second platinum unit.

-

Arai,Halpern

, p. 1571 (1971)

-

Augustine, R. L.,Peppen, J. F. van

, (1970)

Triphenylphosphonium Bromide: A Convenient and Quantitative Source of Gaseous Hydrogen Bromide

Hercouet, A.,Corre, M. Le

, p. 157 - 158 (1988)

Thermolysis of triphenylphosphonium bromide in refluxing xylene provides quantitative yield of anhydrous hydrogen bromide.

Nonterminating alternating copolymerization of ethene with carbon monoxide and the synthesis of graft polymers with alt-ethene-carbon monoxide blocks

Kacker, Smita,Sen, Ayusman

, p. 10591 - 10592 (1995)

-

Synthesis of ruthenium phenylindenylidene, carbyne, allenylidene and vinylmethylidene complexes from (PPh3)3-4RuCl2: A mechanistic and structural investigation

Shaffer, Erika A.,Chen, Chun-Long,Beatty, Alicia M.,Valente, Edward J.,Schanz, Hans-J?rg

, p. 5221 - 5233 (2007)

The reaction of (Ph3P)3RuCl2 with 1,1-diphenyl-2-propyn-1-ol was investigated in various solvents. The reaction in thf under reflux is reported to produce the (PPh3)2Cl2Ru(3-phenylindenylidene) complex (3) which has undergone rearrangement of the allenylidene C3-spine. We have improved the reliability of the reported synthesis by adding acetyl chloride which converts the formed water of the reaction and thus increases the acidity of the reaction solution. Without the additive, we observed the exclusive formation of an intermediate of the transformation and identified it as dinuclear (PPh3)2ClRu(μ-Cl)3(PPh3)2Ru{double bond, long}C{double bond, long}C{double bond, long}CPh2 complex (5). The reaction of (Ph3P)3-4RuCl2 with 1,1-diphenyl-2-propyn-1-ol in CH2Cl2 or C2H4Cl2 under reflux in the presence of excess conc. aqueous HCl afforded the new, neutral (PPh3)2Cl3Ru{triple bond, long}C-CH{double bond, long}CPh2 carbyne complex (7), an HCl adduct of previously elusive (PPh3)2Cl2Ru{double bond, long}C{double bond, long}C{double bond, long}CPh2 complex 6 in high yields. In contrast to the formation of complex 3, the reaction in a non-coordinating solvent did not afford the rearrangement of the allenylidene C3-spine. Complex 7 was converted into complex 3 in thf under reflux under loss of a molecule HCl. Complex 7 was converted with triethylamine under loss of HCl to complex 6. Pentacoordinate complex 6 was crystallized in the presence of O-donor ligands (EtOH, MeOH and H2O) to give hexacoordinate (PPh3)2Cl2(ROH)Ru{double bond, long}C{double bond, long}C{double bond, long}CPh2 (R = H, CH3, C2H5) complexes (9)-(11) with the O-donor coordinating in trans-position to the allenylidene moiety. The reaction of complex 7 with 2 equiv. of 4-(N,N-dimethylamino)pyridine (DMAP) gave hexacoordinate (PPh3)2Cl2(DMAP)Ru{double bond, long}C{double bond, long}C{double bond, long}CPh2complex (12) with one molecule DMAP also coordinating in trans-position to the allenylidene group. Methanol and acetic acid in the absence of strong bases afforded the Fischer-carbene complexes (PPh3)2Cl2Ru{double bond, long}C(OCH3)-CH{double bond, long}CPh2 (14) and (PPh3)2Cl2Ru{double bond, long}C(OAc)-CH{double bond, long}CPh2 (15) where the nucleophile added to the α-carbon atom. The structures of complexes 5, 7, 9-11, 14, and 15 were solved via X-ray crystallography.

Mono-and dihydrophosphoranes and dihydrophosphoranates as intermediates in the reaction of phosphonium salts with LiAiH4

Donoghue, Neil,Gallagher, Michael J.

, p. 169 - 173 (1997)

Reduction of tetraphenylphosphonium bromide with LiAlH(D)4 at room temperature affords first the monohydrophosphorane Ph4PH, then the dihydrophosphoranate anion [Ph4PH2]- which decomposes to the dihydrophosphorane Ph3PH2, all of which are identified by 31PNMR. Reductions of other phosphonium salts appear to follow a similar path. At elevated temperatures none of these intermediates is observed and attempted isolation leads to extensive decomposition.

Coordination Chemistry of Borane in Solution: Application to a STING Agonist

Lemaire, Sébastien,Zhdanko, Alexander,van der Worp, Boris A.

, (2022/04/09)

Equilibrium constants were determined for ligand exchange reactions of borane complexes with various oxygen, sulfur, nitrogen, and phosphorus nucleophiles in solution, and a binding affinity scale was built spanning a range of 12 orders of magnitude. While the Keq are minimally dependent on the solvent, the rate of ligand exchange varies significantly. The fastest and slowest rates were observed in THF and CDCl3, respectively. Moreover, the ligand exchange rate differs in a very broad range depending on stability of the starting complex. Binding of BH3 was found to be much more sensitive to steric factors than protonation. Comparing nitrogen bases having equal steric properties, a linear correlation of BH3 binding affinity vs. Br?nsted acidity was found. This correlation can be used to quickly estimate the BH3 binding affinity of a substrate if pKa is known. Kinetic studies suggest the ligand exchange to occur as a bimolecular SN2 reaction unless other nucleophilic species were present in the reaction mixture.

Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium

Ling, Liang,Luo, Meiming,Tang, Jinghua,Yuan, Shuqing,Zeng, Xiaoming

supporting information, p. 1581 - 1586 (2022/03/14)

We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani

Bis(pertrifluoromethylcatecholato)silane: Extreme Lewis Acidity Broadens the Catalytic Portfolio of Silicon

Thorwart, Thadd?us,Roth, Daniel,Greb, Lutz

supporting information, p. 10422 - 10427 (2021/05/27)

Given its earth abundance, silicon is ideal for constructing Lewis acids of use in catalysis or materials science. Neutral silanes were limited to moderate Lewis acidity, until halogenated catecholato ligands provoked a significant boost. However, catalytic applications of bis(perhalocatecholato)silanes were suffering from very poor solubility and unknown deactivation pathways. In this work, the novel per(trifluoromethyl)catechol, H2catCF3, and adducts of its silicon complex Si(catCF3)2 (1) are described. According to the computed fluoride ion affinity, 1 ranks among the strongest neutral Lewis acids currently accessible in the condensed phase. The improved robustness and affinity of 1 enable deoxygenations of aldehydes, ketones, amides, or phosphine oxides, and a carbonyl-olefin metathesis. All those transformations have never been catalyzed by a neutral silane. Attempts to obtain donor-free 1 attest to the extreme Lewis acidity by stabilizing adducts with even the weakest donors, such as benzophenone or hexaethyl disiloxane.

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