147531-11-1

Basic information

• Product Name: diphenyl-(trifluoromethyl)-sulfonium trifluoromethanesulfonate
• Synonyms: diphenyl-(trifluoromethyl)-sulfonium trifluoromethanesulfonate;diphenyl-(trifluoroMethyl)-sulfoniuM;Diphenyl-(trifluoroMethyle)-sulfoniuM trifluoroMethancesulfonate;(S)-(trifluoroMethyl)diphenylsulfoniuM triflate;diphenyl(trifluoromethyl)sulfanium trifluoromethanesulfonate;Diphenyl(trifluoromethyl);sulfonium trifluoromethanesulfonate;diphenyl(trifluoromethyl)sulfanium
• CAS NO: 147531-11-1
• Molecular Formula: C13H10F3S.CF3O3S
• Molecular Weight: 404.35
• Mol File: 147531-11-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 84-85 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: diphenyl-(trifluoromethyl)-sulfonium trifluoromethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenyl-(trifluoromethyl)-sulfonium trifluoromethanesulfonate(147531-11-1)
• EPA Substance Registry System: diphenyl-(trifluoromethyl)-sulfonium trifluoromethanesulfonate(147531-11-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 147531-11-1(Hazardous Substances Data)

Usage

Uses

Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate

InChI:InChI=1/C13H10F3S.CHF3O3S/c14-13(15,16)17(11-7-3-1-4-8-11)12-9-5-2-6-10-12;2-1(3,4)8(5,6)7/h1-10H;(H,5,6,7)/q+1;/p-1

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 703-18-4 phenyl trifluoromethyl sulfoxide 
• 71-43-2 benzene 
• 41804-89-1 potassium triflinate 
• 2926-29-6 Langlois reagent 
• 456-56-4 phenyl trifluoromethylsulfide 

Downstream Products

• 56734-74-8 2-(trifluoromethyl)cyclohexanone 
• 51310-55-5 3-(trifluoromethyl)-1H-indole 
• 2008-04-0 2-(trifluoromethyl)benzo[d]oxazole 
• 258506-68-2 3-chloro-6-(trifluormethyl)pyridazine 
• 384-46-3 1-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazole 
• 145914-06-3 1,1,1-trifluoro-2-(2-nitrophenyl)ethane 
• 65715-20-0 2-(trifluoromethyl)benzofuran 
• 25199-76-2 3-(trifluoromethyl)quinoline 
• 772-62-3 3,3,3-trifluoro-1-phenylpropyne 
• 127300-01-0 1-propyl-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 
• 1227931-82-9 1-(tert-butyl)-4-(3,3,3-trifluoroprop-1-yn-1-yl)-benzene 
• 82203-83-6 1-(p-methoxyphenyl)-3,3,3-trifluoropropyne 
• 1464776-39-3 1-ethoxy-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 
• 7119-09-7 1-bromo-4-(3,3,3-trifluoro-1-propyn-1-yl)benzene 

Relevant articles and documents

New Electrophilic Trifluoromethylating Agents

Synthetic routes to S-(trifluoromethyl)phenyl-4-fluorophenylsulfonium triflate (8), S-(trifluoromethyl)phenyl-2,4-difluorophenylsulfonium triflate (9), S-(trifluoromethyl)phenyl-3-nitrophenylsulfonium triflate (10), and S-(trifluoromethyl)-4-fluorophenyl-3-nitrophenylsulfonium triflate (11) are described. They are stable molecules and conveniently prepared by treating phenyl trifluoromethyl sulfoxide with benzene and its derivatives. These novel electrophilic trifluoromethylating agents react under mild conditions with a variety of aromatic rings (p-hydroquinone, pyrrole, and aniline) to give trifluoromethylated compounds (2-trifluoromethyl-p-hydroquinone, 2-trifluoromethylpyrrole, 2-trifluoromethylaniline, and 4-trifluoromethylaniline) in moderate to high yields. The electrophilic trifluoromethylating potential can be altered by placing electron-withdrawing substituents on the benzene rings.

Visible-Light Photocatalytic Tri- A nd Difluoroalkylation Cyclizations: Access to a Series of Indole[2,1- A[isoquinoline Derivatives in Continuous Flow

A process for achieving photocatalyzed tri- A nd difluoromethylation/cyclizations for constructing a series of tri-or difluoromethylated indole[2,1-a]isoquinoline derivatives is described. This protocol utilized an inexpensive organic photoredox catalyst and provided good yields. Moreover, the combination of continuous flow and photochemistry, designed to provide researchers with a unique green process, was also shown to be key to allowing the reaction to proceed (product yield of 83% in flow vs 0% in batch).

Palladium-Catalyzed Arylation of Arylboronic Acids with Yagupolskii-Umemoto Reagents

A Pd-catalyzed Suzuki cross-coupling of arylboronic acids with Yagupolskii-Umemoto reagents was explored. In contrary to trifluoromethylations, the Pd-catalyzed reaction of R-B(OH)2 and [Ar2SCF3]+[OTf]- provided the arylation products (R-Ar) in good to high yields. The reaction confirms that the S-Ar bonds of [Ar2SCF3]+[OTf]- can be readily cleaved in the presence of Pd complexes. The relatively electron-poor aryl groups of asymmetric [Ar1Ar2SCF3]+[OTf]- salts are more favorably transferred compared to the electron-rich ones. This reaction represents the first report of utilization of [Ar2SCF3]+[OTf]- as arylation reagents in organic synthesis.

Photoredox-Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated Alkenes

A regio- and stereoselective synthesis of trifluoromethylated alkenes bearing four different substituents has been developed. Stereocontrolled sulfonyloxytrifluoromethylation of unsymmetric internal alkynes with an electrophilic CF3 reagent, namely the triflate salt of the Yagupol'skii-Umemoto reagent, in the presence of an Ir photoredox catalyst under visible-light irradiation afforded trifluoromethylalkenyl triflates with well-predictable stereochemistry resulting from anti addition of the trifluoromethyl and triflate groups. Subsequent palladium-catalyzed cross-couplings led to tetrasubstituted trifluoromethylated alkenes in a highly stereoselective manner. The present method is the first example of a facile one-pot synthesis of tetrasubstituted trifluoromethylated alkenes from simple alkynes.