Chemistry Organic Building Blocks Trifluoromethanesulfonate
Triflate (systematic name: trifluoromethanesulfonate) is a common functional group in organic chemistry with the general structure R−O−S(=O)2−CF3. The abbreviation -OTf is often used to represent the triflate group, whereas -Tf refers to the triflyl group, R−SO2CF3.
Triflate, also known as trifluoromethanesulfonate, is a highly effective leaving group that finds application in a variety of organic reactions, including nucleophilic substitution, Suzuki couplings, and Heck reactions.
Due to their high reactivity in SN2 reactions, alkyl triflates must be stored under anhydrous conditions to prevent the presence of nucleophiles, such as water.
The stability of the anion is attributed to resonance stabilization, which distributes the negative charge evenly over the three oxygen atoms. The trifluoromethyl group, acting as a potent electron-withdrawing group through the sulfur bridge, further enhances this stability.
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Cyclohept-1-en-1-yl trifluoromethanesulfonate
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Ethyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate
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2,2,3,3,3-Pentafluoropropyl trifluoromethanesulfonate
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Ethyl 2-(4-(trifluoromethylsulfonyloxy)cyclohex-3-enyl)acetate
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Cyclohex-1-en-1-yl trifluoromethanesulfonate
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Tetrahydro-2H-pyran-4-yl trifluoromethanesulfonate
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(1-Methylcyclohexyl)methyl trifluoromethanesulfonate