215438-84-9

Basic information

• Product Name: methyl diphenylsulfonium triflate
• Synonyms: methyl diphenylsulfonium triflate
• CAS NO: 215438-84-9
• Molecular Weight: 364.41
• Mol File: 215438-84-9.mol

Chemical Properties

• CAS DataBase Reference: methyl diphenylsulfonium triflate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl diphenylsulfonium triflate(215438-84-9)
• EPA Substance Registry System: methyl diphenylsulfonium triflate(215438-84-9)

Safety Data

• Hazardous Substances Data: 215438-84-9(Hazardous Substances Data)

Upstream product

• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 1493-13-6 trifluorormethanesulfonic acid 
• 139-66-2 diphenyl sulfide 
• 109-94-4 formic acid ethyl ester 
• 141-78-6 ethyl acetate 

Downstream Products

• 1227796-83-9 phenyl (pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1227796-88-4 (4-methylphenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1227796-85-1 (4-methoxyphenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1227796-87-3 (4-fluorophenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1227796-84-0 (4-chlorophenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1443994-87-3 (4-bromophenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1443994-88-4 (2-fluorophenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1443994-90-8 (2-chlorophenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1443994-91-9 (3-chlorophenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 1443994-92-0 (2,4-dichlorophenyl)(pyrrolo[2,1-a]isoquinolin-3-yl)methanone 
• 105229-70-7 methyldiphenylsulfonium trifluoromethanesulfonate 
• 7380-78-1 4-(phenylethynyl)anisole 
• 37696-01-8 1-methoxy-3-(phenylethynyl)benzene 
• 41398-67-8 2-phenylethynylanisole 

Relevant articles and documents

Sonogashira reaction using arylsulfonium salts as cross-coupling partners

Triarylsulfonium, alkyl- and fluoroalkyl(diaryl)-sulfonium, and aryl(dialkyl)sulfonium triflates are successfully used as a new family of cross-coupling participants in the Sonogashira reaction as aryldiazonium, diaryliodonium, and tetraphenylphosphonium salts. It was found that terminal alkynes reacted mildly with triarylsulfonium or (2,2,2-trifluoroethyl)diphenylsulfonium triflate at room temperature under Pdand Cu-cocatalysis to give the corresponding arylalkynes in up to >99% yield. This protocol represents the first use of arylsulfonium salts as cross-coupling partners in the Pd/Cu-catalyzed Sonogashira reaction.

Pd-catalyzed Suzuki–Miyaura cross-coupling of [Ph2SR][OTf] with arylboronic acids

The Pd-catalyzed Suzuki–Miyaura cross-coupling of alkyl- and fluoroalkyl(diphenyl)sulfonium triflates with arylboronic acids was compared. The fluorine substitution on the alkyl groups of [Ph2SR][OTf] had a big influence on the reaction. Perfluoroalkyl(diphenyl)sulfonium triflates (2b–d) were unsuccessful participants in the Pd-catalyzed phenylation of arylboronic acid under the standard conditions because of the strong electronegativity of the long-chain perfluoroalkyl groups, which underwent S[sbnd]Rfnbond cleavage instead. Polyfluoroalkyl(diphenyl)sulfonium triflates (2f–h) reacted with arylboronic acid to afford the phenylation product in very low yields due to the tendency of deprotonation and β-F elimination of the sulfonium salts. Eventually, (2,2,2-trifluoroethyl)diphenylsulfonium triflate (2e), methyl- or ethyl(diphenyl)sulfonium triflate (2i or 2j), and triphenylsulfonium triflate (2m) were found to be more effective reagents than other tested phenylsulfounium salts for Pd-catalyzed phenylation, which provided much higher yields of the desired products under mild conditions.