Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem CID
Reaxys RN
Diphenyl(trifluoromethyl)sulfonium triflate,[Ph2SCF3]+[OTf]-
Trifluoromethylating Reagents
KUMI6F09
147531-11-1
MFCD12912173
18401167
6171037
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay
Appearance
Melting Point
Packaging
Storage
Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate
C14H10F6O3S2
404.35
≥98.0%
White to Yellow Solid
85-86°C
5g,10g,25g,50g,100g and 500g
Store at room temperature
Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate(Ph2SCF3]+[OTf]-) is a versatile,shelf-stable reagent for electrophilic trifluoromethylation of various nucleophiles, such as heteroaromatic compounds,benzyl bromides,arylboronic acids,terminal alkynes,α,β-unsaturated ketones and propargyl acetates, etc.. It reacts with Na2S2O4 or HOCH2SO2Na under suitable conditions to generate CF3 radical for the synthesis of α-trifluoromethylated ketones.
Power-variable electrophilic trifluoromethylating agents. S-, Se-, and Te-(trifluoromethyl)dibenzothio-, -seleno-, and -tellurophenium salt system. [1]
New Method for Trifluoromethylation of Enolate Anions and Applications to Regio-, Diastereo- and Enantioselective Trifluoromethylation. [2]
Kinetic study of trifluoromethylation with S-(trifluoromethyl) dibenzothiophenium salts. [3]
New Electrophilic Trifluoromethylating Agents. [4]
Straightforward one-pot synthesis of trifluoromethyl sulfonium salts. [5]
Benchmark and Solvent-Free preparation of sulfonium salt based electrophilic trifluoromethylating reagents. [6]
Copper-mediated trifluoromethylation of heteroaromatic compounds by trifluoromethyl sulfonium salts. [7]
Generation of the CF3 radical from trifluoromethylsulfonium triflate and its trifluoromethylation of styrenes. [8]
Cu-mediated chemoselective trifluoromethylation of benzyl bromides using shelf-stable electrophilic trifluoromethylating reagents. [9]
Copper-mediated trifluoromethylation of arylboronic acids by trifluoromethyl sulfonium salts. [10]
Copper-mediated trifluoromethylation of terminal alkynes by S-(trifluoromethyl)diarylsulfonium salt. [11]
Regioselective 1,4-trifluoromethylation of α,β-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system. [12]
Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent. [13]
Copper-mediated trifluoromethylation of propargyl acetates leading to trifluoromethyl-allenes. [14]
Palladium-Catalyzed Arylation of Arylboronic Acids with Yagupolskii-Umemoto Reagents. [15]
Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature. [16]
Pd-catalyzed Suzuki–Miyaura cross-coupling of [Ph2SR][OTf] with arylboronic acids. [17]
Cu-Mediated Trifluoromethylation of Aromatic α-Diazo Esters with the Yagupolskii–Umemoto Reagent. [18]
References:
[1] T.Umemoto, et al, J. Am. Chem. Soc., 1993, 115(6), pp 2156-2164.
[2] T.Umemoto, et al, J. Org. Chem., 1994, 59(19), pp 5692-5699.
[3] T.Ono, et al, J. F. Chem, 1996, 80(2), pp 163-166.
[4] J.J.Yang, et al, J. Org. Chem., 1998, 63(8), pp 2656-2660.
[5] E.Magnier, et al, Angew. Chem. Int. Ed., 2006, 45(8), pp 1279-1282.
[6] Y.Mace, et al, Eur. J. Org. Chem., 2009, 9, pp 1390-1397.
[7] C.P.Zhang, et al, Angew. Chem. Int. Ed., 2011, 50(8), pp 1896-1900.
[8] C.P.Zhang, et al, Chem. Commun., 2011, 47(23), pp 6632-6634.
[9] H.Kawai, et al, Org. Lett., 2011, 13(14), pp 3596-3599.
[10] C.P.Zhang, et al, Chem. Commun., 2011, 47(33), pp 9516-9518.
[11] X.Wang, et al, Chin. J. Chem., 2013, 31(7), pp 915-920.
[12] S.Okusu, et al, Beilstein J. Org. Chem., 2013, 9, pp 2189-2193.
[13] X.P.Wang, et al, Beilstein, J. Org. Chem., 2013, 9, pp 2635-2640.
[14] Y.L.Ji, et al, Org. Biomol. Chem., 2014, 12(18), pp 2903-2906.
[15] S.M.Wang, et al, Chem. Eur. J., 2016, 22(19), pp 6542-6546.
[16] S.M.Wang, et al, Chem. Commun., 2016, 52(80), pp 11893-11896.
[17] X.Y.Wang, et al, Tetrahedron, 2016, 72(47), pp 7606-7612.
[18] X.Q.Hu, et al, Eur. J. Org. Chem, 2017, 2, pp 324-331.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
Warning
H315,H319,H335
P280,P305+P351+P338
29049900
NONH for all modes of transport

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