329685-39-4

Basic information

• Product Name: Methanesulfonic acid, trifluoro-, 4-(phenylmethyl)phenyl ester
• CAS NO: 329685-39-4
• Molecular Formula: C14H11F3O3S
• Molecular Weight: 316.301
• Mol File: 329685-39-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methanesulfonic acid, trifluoro-, 4-(phenylmethyl)phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid, trifluoro-, 4-(phenylmethyl)phenyl ester(329685-39-4)
• EPA Substance Registry System: Methanesulfonic acid, trifluoro-, 4-(phenylmethyl)phenyl ester(329685-39-4)

Safety Data

• Hazardous Substances Data: 329685-39-4(Hazardous Substances Data)

Upstream product

• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 109586-39-2 4-iodophenyl trifluoromethanesulfonate 
• 101-53-1 p-benzylphenol 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 35444-94-1 1-benzyl-4-iodobenzene 
• 911708-01-5 2-(4-benzylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 613-42-3 4-benzylbiphenyl 
• 101-81-5 Diphenylmethane 

Relevant articles and documents

Transition-Metal-Free C-C, C-O, and C-N Cross-Couplings Enabled by Light

Transition-metal-catalyzed cross-couplings to construct C-C, C-O, and C-N bonds have revolutionized chemical science. Despite great achievements, these metal catalysts also raise certain issues including their high cost, requirement of specialized ligands, sensitivity to air and moisture, and so-called "transition-metal-residue issue". Complementary strategy, which does not rely on the well-established oxidative addition, transmetalation, and reductive elimination mechanistic paradigm, would potentially eliminate all of these metal-related issues. Herein, we show that aryl triflates can be coupled with potassium aryl trifluoroborates, aliphatic alcohols, and nitriles without the assistance of metal catalysts empowered by photoenergy. Control experiments reveal that among all common aryl electrophiles only aryl triflates are competent in these couplings whereas aryl iodides and bromides cannot serve as the coupling partners. DFT calculation reveals that once converted to the aryl radical cation, aryl triflate would be more favorable to ipso substitution. Fluorescence spectroscopy and cyclic voltammetry investigations suggest that the interaction between excited acetone and aryl triflate is essential to these couplings. The results in this report are anticipated to provide new opportunities to perform cross-couplings.

Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates.

[figure: see text] The palladium-catalyzed coupling reaction of potassium alkyltrifluoroborates with aryl- or alkenyltriflates proceeds to afford the corresponding arenes or alkenes in high yield. The borates are all solids, stable in air, and thus can be stored on the shelf indefinitely. The cross coupling can be effected using PdCl2(dppf).CH2Cl2 as the catalyst in THF-H2O in the presence of Cs2CO3. A variety of functional groups can be tolerated within the borate and/or the triflate coupling partner.