2613-27-6

Basic information

• Product Name: 4-NITROPHENYLSULFUR PENTAFLUORIDE
• Synonyms: SULFUR, PENTAFLUORO(4-NITROPHENYL)-;4-NITROPHENYLSULFUR PENTAFLUORIDE;4-NITROPHENYLSULPHUR PENTAFLUORIDE;4-NITROBENZENESULFURPENTAFLUORIDE;4-(PENTAFLUOROSULFUR)-NITROBENZENE;1-NITRO-4-(PENTAFLUOROSULFANYL)BENZENE;BUTTPARK 19\10-04;4-Nitrobenzenesulphur pentafluoride
• CAS NO: 2613-27-6
• Molecular Formula: C₆H₄F₅NO₂S
• Molecular Weight: 249.16
• EINECS: 447-610-7
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 2613-27-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 38 °C
• Boiling Point: 76-77°C 12mm
• Flash Point: 76-77°C/12mm
• Appearance: /
• Density: g/cm³
• Refractive Index: 1.4729
• Water Solubility: Insoluble in water
• BRN: 1986023
• CAS DataBase Reference: 4-NITROPHENYLSULFUR PENTAFLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROPHENYLSULFUR PENTAFLUORIDE(2613-27-6)
• EPA Substance Registry System: 4-NITROPHENYLSULFUR PENTAFLUORIDE(2613-27-6)

Safety Data

• Hazard Codes: Xi,T
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• TSCA: No
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2613-27-6(Hazardous Substances Data)

Usage

General Description

4-Nitrophenylsulfur pentafluoride is a chemical compound with the molecular formula C6H4F5NO2S. It is an organofluorine compound that is commonly used as a fluorinating agent in organic synthesis. This molecule is a powerful electrophilic fluorinating reagent that can be used to introduce fluorine atoms into organic compounds, particularly aromatic and heteroaromatic compounds. It is often utilized in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. 4-Nitrophenylsulfur pentafluoride is known for its high reactivity and selectivity in fluorination reactions, making it a valuable tool in the field of organic chemistry. However, it should be handled with caution due to its potential toxicity and corrosiveness.

InChI:InChI=1/C6H4F5NO2S/c7-15(8,9,10,11)6-3-1-5(2-4-6)12(13)14/h1-4H

Synthetic route

4-nitrophenyltetrafluoro-λ6-sulfanyl chloride → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6)

Conditions	Yield
With hydrogen fluoride; mercury(II) oxide at -30 - 20℃; Inert atmosphere; Sealed tube;	81%
With iodine pentafluoride In neat (no solvent) at 65℃; for 14h; Glovebox; Inert atmosphere;	75%
With silver carbonate at 70℃; Inert atmosphere; Glovebox;	66%
With zinc(II) fluoride at 150℃; for 72h; Inert atmosphere;	36%
With silver tetrafluoroborate In dichloromethane at 20℃; for 14h; Inert atmosphere;	189.9 mg

di(p-nitrophenyl) disulfide (100-32-3) → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6)

Conditions	Yield
With potassium fluoride; bis(fluoroxy)methane at -20 - -15℃;	63%
With silver(II) fluoride In various solvent(s) at 20 - 130℃;	50%
With fluorine In acetonitrile at -5℃; for 1h; Inert atmosphere;	45%

4-nitrophenylsulphur trifluoride (1526-28-9) → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6)

Conditions	Yield
With fluorine In acetonitrile at 20℃;	60%
With fluorine Ambient temperature;	44%
With bis(fluoroxy)methane In acetonitrile at -20 - 20℃;
With fluorine; cesium fluoride In acetonitrile at -30 - -25℃;
With potassium fluoride; bis(fluoroxy)methane In acetonitrile at -15℃;

para-nitrobenzenethiol (1849-36-1) → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6)

Conditions	Yield
In acetonitrile	28%
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 0.5 h / Inert atmosphere 1.2: 14 h / 20 °C / Inert atmosphere 2.1: potassium fluoride; chlorine / acetonitrile / 20 °C / Inert atmosphere; Glovebox; Cooling with ice 3.1: iodine pentafluoride / neat (no solvent) / 14 h / 65 °C / Glovebox; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 0.5 h / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: potassium fluoride; chlorine / acetonitrile / 20 °C / Inert atmosphere; Glovebox; Cooling with ice 3.1: silver carbonate / 70 °C / Inert atmosphere; Glovebox View Scheme

4-nitrobenzenesulfenyl chloride (937-32-6) → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6)

Conditions	Yield
Stage #1: 4-nitrobenzenesulfenyl chloride With bis(fluoroxy)methane In acetonitrile at -20 - -15℃; Stage #2: With cesium fluoride In acetonitrile
Stage #1: 4-nitrobenzenesulfenyl chloride With bis(fluoroxy)methane In acetonitrile at -20 - -15℃; Stage #2: With fluorine; cesium fluoride In acetonitrile at -30 - -25℃;
Multi-step reaction with 2 steps 1: potassium fluoride; chlorine / acetonitrile / 5 - 11 °C 2: zinc(II) fluoride / 72 h / 150 °C / Inert atmosphere View Scheme

di(p-nitrophenyl) disulfide (100-32-3) → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + 4-nitrophenylsulphur trifluoride (1526-28-9)

Conditions	Yield
With fluorine In acetonitrile at -35 - -25℃;

di(p-nitrophenyl) disulfide (100-32-3) → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + 4-nitrobenzenesulfonyl fluoride (349-96-2)

Conditions	Yield
With silver(II) fluoride; copper at 60 - 125℃; for 8h; Sealed tube;	A 6.73 g B n/a

4-Fluoronitrobenzene (350-46-9) → 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium sulfide / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / water / 0.5 h / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: potassium fluoride; chlorine / acetonitrile / 20 °C / Inert atmosphere; Glovebox; Cooling with ice 4.1: silver carbonate / 70 °C / Inert atmosphere; Glovebox View Scheme

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 4-(pentafluorosulfanyl)aniline (2993-24-0)

Conditions	Yield
With hydrogenchloride; iron In ethanol; water at 0 - 20℃; for 1h;	100%
With hydrogen; nickel In ethanol	99%
Stage #1: 1-nitro-4-(pentafluorosulfanyl)benzene With hydrogenchloride; tin(ll) chloride In water at 45 - 100℃; for 3.5h; Stage #2: With sodium hydroxide In dichloromethane; water at 0℃;	99%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + benzyl alcohol (100-51-6) → (4-(benzyloxy)phenyl)pentafluoro-λ6-sulfane (1126968-88-4)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	96%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h;	96%

meta-bromotoluene (591-17-3) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 3,3''-dimethyl-2'-nitro-[1,1':3',1''-terphenyl]-5'-yl sulfurpentafluoride

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 2,2-dimethylbutyric acid; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 130℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube;	95%

3-methoxyphenyl bromide (2398-37-0) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 3,3''-dimethoxy-2'-nitro-[1,1':3',1''-terphenyl]-5'-yl sulfurpentafluoride

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 2,2-dimethylbutyric acid; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 130℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube;	92%

tert-Butyl chloroacetate (107-59-5) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → tert-butyl [2-nitro-5-(pentafluoro-λ6-sulfanyl)phenyl]acetate (1309569-24-1)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; for 0.166667h;	91%
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; for 0.166667h; Vicarious Nucleophilic Substitution;	80%
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; Inert atmosphere;	38%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 2-nitro-5-(pentafluorosulfanyl)phenol (1329120-21-9)

Conditions	Yield
With Cumene hydroperoxide; potassium tert-butylate; methylamine In tetrahydrofuran at -78 - -50℃; for 0.5h;	91%
With Cumene hydroperoxide; potassium tert-butylate; methylamine In tetrahydrofuran at -50℃; for 0.25h;	90%
With Cumene hydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran at -50℃; for 0.25h;	76%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + sodium methylate (124-41-4) → 1-methoxy-4-(pentafluorosulfanyl)-benzene

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h;	87%
In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	83%
In N,N-dimethyl-formamide at 20℃; for 1h;	83%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + chloromethyl phenyl sulfone (7205-98-3) → pentafluoro(4-nitro-3-((phenylsulfonyl)methyl)phenyl)-λ6-sulfane (1309569-14-9)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at -40℃; for 0.166667h; Vicarious Nucleophilic Substitution;	87%
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; for 0.5h; Inert atmosphere;	86%
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; for 0.5h;	86%
With potassium tert-butylate In N,N-dimethyl-formamide at -40℃; for 0.5h;	84%
With potassium tert-butylate In N,N-dimethyl-formamide at -40℃; for 0.5h;	84%

bromobenzene (108-86-1) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 2'-nitro-[1,1':3',1''-terphenyl]-5'-yl sulfurpentafluoride + 6-nitro-[1,1'-biphenyl]-3-yl sulfurpentafluoride

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 2,2-dimethylbutyric acid; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 130℃; for 15h; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;	A 87% B 4%
With bis(η3-allyl-μ-chloropalladium(II)); 2,2-dimethylbutyric acid; caesium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 130℃; for 12h; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;	A 18 %Spectr. B 41 %Spectr.

Ethyl 4-bromobenzoate (5798-75-4) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → diethyl 5'-(pentafluorothio)-2'-nitro-[1,1':3',1''-terphenyl]-4,4''-dicarboxylate + C15H12F5NO4S

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 2,2-dimethylbutyric acid; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 130℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube;	A 86% B 5%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 2-bromo-4-(pentafluoro-λ6-sulfanyl)aniline (159727-25-0)

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 3 - 20℃; for 2h;	85%
Multi-step reaction with 2 steps 1: 99 percent / H2 / Raney nickel / ethanol 2: NBS / acetonitrile / 0 °C View Scheme

diethyl chloromethylphosphonate (3167-63-3) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → diethyl 2-nitro-5-(pentafluorosulfanyl)benzylphosphonate (1309569-28-5)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at -60℃; for 0.166667h;	84%
With potassium tert-butylate In N,N-dimethyl-formamide at -60℃; for 0.5h; Vicarious Nucleophilic Substitution;	77%
Stage #1: diethyl chloromethylphosphonate; 1-nitro-4-(pentafluorosulfanyl)benzene With potassium tert-butylate In N,N-dimethyl-formamide at -60℃; for 0.166667h; Stage #2: With water Acidic conditions;

octanol (111-87-5) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 1-(n-octyloxy)-4-(pentafluorosulfanyl)benzene (1272542-14-9)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.3h; Inert atmosphere;	83%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.333333h;	83%

dichloroacetic acid methyl ester (116-54-1) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → C9H7ClF5NO4S (1309569-25-2)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; for 0.166667h;	83%

4-biphenylacetonitrile (31603-77-7) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 3-(biphenyl-4-yl)-5-(pentafluorosulfanyl)benzo[c]isoxazole (1440512-00-4)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 1h;	83%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 2-nitro-5-(pentafluorosulfanyl)aniline (1379803-65-2)

Conditions	Yield
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide at 20℃; for 0.0833333h;	82%
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide	82%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + 4-Ethynylaniline (14235-81-5) → N-(4-ethynylphenyl)-2-nitro-5-(pentafluorosulfanyl)aniline

Conditions	Yield
Stage #1: 4-Ethynylaniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0166667h; Inert atmosphere; Stage #2: 1-nitro-4-(pentafluorosulfanyl)benzene In tetrahydrofuran; hexane at -120 - -110℃; for 0.166667h; Inert atmosphere; Stage #3: With potassium permanganate; ammonia In tetrahydrofuran; hexane at -110℃; for 0.0833333h; Inert atmosphere;	78%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + chloroacetic acid ethyl ester (105-39-5) → C10H10F5NO4S (1309569-23-0)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; for 0.166667h;	76%
With potassium tert-butylate In N,N-dimethyl-formamide at -30℃; for 0.166667h;	76%

chloroform (67-66-3) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 2-(dichloromethyl)-1-nitro-4-(pentafluorosulfanyl)benzene (1309569-30-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; chloroform; N,N-dimethyl-formamide at -78℃; for 0.5h; Inert atmosphere;	75%
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -70℃; for 0.0333333h;	74%

2-bromonaphthalene (580-13-2) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → diethyl 5'-(pentafluorothio)-2'-nitro-[1,1':3',1''-terphenyl]-4,4''-dicarboxylate + C16H10F5NO2S

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 2,2-dimethylbutyric acid; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 130℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube;	A 75% B 17%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + sodium ethanolate (141-52-6) → 1-ethoxy-4-(pentafluorosulfanyl)benzene (1272542-12-7)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	74%
In N,N-dimethyl-formamide at 20℃; for 1h;	74%

Bromoform (75-25-2) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → C7H4Br2F5NO2S (1309569-31-0)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -70℃; for 0.0333333h;	74%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + phenoxyacetonitrile (3598-14-9) → 2-(2-nitro-5-(pentafluorosulfanyl)phenyl)acetonitrile (1309569-29-6)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.166667h;	74%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.166667h;	74%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.5h; Vicarious Nucleophilic Substitution;	41%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + aniline (62-53-3) → 2-nitro-5-(pentafluorosulfanyl)-N-phenylaniline

Conditions	Yield
Stage #1: aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0166667h; Inert atmosphere; Stage #2: 1-nitro-4-(pentafluorosulfanyl)benzene In tetrahydrofuran; hexane at -120 - -110℃; for 0.166667h; Inert atmosphere; Stage #3: With potassium permanganate; ammonia In tetrahydrofuran; hexane at -110℃; for 0.0833333h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	73%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + p-toluidine (106-49-0) → 2-nitro-5-(pentafluorosulfanyl)-N-p-tolylaniline

Conditions	Yield
Stage #1: p-toluidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0166667h; Inert atmosphere; Stage #2: 1-nitro-4-(pentafluorosulfanyl)benzene In tetrahydrofuran; hexane at -120 - -110℃; for 0.166667h; Inert atmosphere; Stage #3: With potassium permanganate; ammonia In tetrahydrofuran; hexane at -110℃; for 0.0833333h; Inert atmosphere;	73%

1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) + 4-chloro-aniline (106-47-8) → N-(4-chlorophenyl)-2-nitro-5-(pentafluorosulfanyl)aniline

Conditions	Yield
Stage #1: 4-chloro-aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0166667h; Inert atmosphere; Stage #2: 1-nitro-4-(pentafluorosulfanyl)benzene In tetrahydrofuran; hexane at -120 - -110℃; for 0.166667h; Inert atmosphere; Stage #3: With potassium permanganate; ammonia In tetrahydrofuran; hexane at -110℃; for 0.0833333h; Inert atmosphere;	72%

propan-1-ol (71-23-8) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 1-(n-propoxy)-4-(pentafluorosulfanyl)benzene (1272542-13-8)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;	71%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.5h;	71%

para-bromotoluene (106-38-7) + 1-nitro-4-(pentafluorosulfanyl)benzene (2613-27-6) → 4,4''-dimethyl-2'-nitro-[1,1':3',1''-terphenyl]-5'-yl sulfurpentafluoride

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 2,2-dimethylbutyric acid; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In toluene at 130℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube;	71%

Upstream product

• 350-46-9 4-Fluoronitrobenzene 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 1849-36-1 para-nitrobenzenethiol 
• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 1526-28-9 4-nitrophenylsulphur trifluoride 

Downstream Products

• 1309569-21-8 tert-butyl [2-amino-5-(pentafluoro-λ⁶-sulfanyl)phenyl]acetate 

Relevant articles and documents

AgBF4-Mediated Chlorine-Fluorine Exchange Fluorination for the Synthesis of Pentafluorosulfanyl (Hetero)arenes

We report a new protocol to form pentafluorosulfanyl (hetero)arenes via chlorine-fluorine exchange of (hetero)aryl tetrafluorosulfanyl chlorides by AgBF4. The method enables access to electron-deficient pentafluorosulfanyl(hetero)arenes, which are targets that are difficult to synthesize. Two advantages of AgBF4 are its ease of handling and stability. This would be a general transformation protocol.

METHOD OF PRODUCING PENTAFLUOROSULFANYL AROMATIC COMPOUND

A method of producing a pentafluorosulfanyl aromatic compound is provided. A method of producing a pentafluorosulfanyl aromatic compound represented by general formula (3): [in-line-formulae]Ar—(SF5)k??(3)[/in-line-formulae]where Ar is a substituted or an unsubstituted aryl group or heteroaryl group, and k is an integer of 1 to 3;the method includes reacting IF5 with a halotetrafluorosulfanyl aromatic compound represented by general formula (2): [in-line-formulae]Ar—(SF4Hal)k??(2)[/in-line-formulae]where Ar and k are defined as above; and Hal is a Cl group, a Br group, or an I group.

Silver-induced self-immolative Cl-F exchange fluorination of arylsulfur chlorotetrafluorides: Synthesis of arylsulfur pentafluorides

A novel strategy for the synthesis of arylsulfur pentafluorides by silver carbonate-induced Cl-F exchange fluorination of arylsulfur chlorotetrafluorides is reported. This fluorination does not require any exogenous fluoride sources. Rather, the reaction proceeds via the self-immolation of the substrate Ar-SF4Cl.