Scandium trifluoromethanesulfonate, commonly called scandium triflate, is a chemical compound with formula Sc(SO₃CF₃)₃, a salt consisting of scandium

cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

s Sc³⁺ and triflate anions. Scandium triflate is used as a reagent in organic chemistry as a

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...

. Compared to other Lewis acids, this reagent is stable towards water and can often be used in

organic reaction Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, Mechanistic Organ ...

s as a true catalyst rather than one used in stoichiometric amounts. The compound is prepared by reaction of scandium oxide with trifluoromethanesulfonic acid. An example of the scientific use of scandium triflate is the Mukaiyama aldol addition reaction between

benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. It is a colorless liquid with a characteristic almond-like odor. ...

and the silyl enol ether of

cyclohexanone Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohexan ...

with an 81% yield. : ScOTf3-mediated aldol condensation transp

References

{{Scandium compounds Scandium compounds Triflates Acid catalysts

See also

References