US 11,840,504 B2Granted

Method for preparing perfluoroalkyl sulfinate ester

AssigneeSoochow University

InventorsXiaobing Wan, Hanghang Wang

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Abstract

The present invention discloses a method for preparing a perfluoroalkyl sulfinate ester. The method includes reacting an α-carbonyldiazo compound and a sodium perfluoroalkyl sulfinate, in an organic solvent, in the presence of anhydrous copper acetate as an optimal catalyst and tert-butyl hydroperoxide (TBHP) as a green oxidant, to obtain the perfluoroalkyl sulfinate ester. Compared to the prior art, the present method has the advantages of a wide range of reaction substrates, a short reaction time, a high reaction yield, and mild reaction conditions. The reaction does not require pre-activation of sodium perfluoroalkyl sulfinate, which can participate in the reaction directly, making reaction operations simple. The present method uses TBHP as a green oxidant and produces tert-butanol and water after reaction. Moreover, the present method avoids using a bromide or a chloride as a reaction material, and thus avoids formation of a large amount of a halide salt.

Claims5

Dependent claims

A method for preparing a perfluoroalkylsulfinate ester, comprising:

reacting an α-carbonyldiazo compound with a sodium perfluoroalkylsulfinate in the presence of a transition metal compound as a catalyst, with a peroxide as an oxidant, in an organic solvent, to obtain the perfluoroalkylsulfinate ester,
wherein the α-carbonyldiazo compound has the following chemical structural formula:
R1 is selected from the group consisting of naphthyl, thienyl, alkyl, alkoxy, and phenol;
or R1 is
R2 is selected from the group consisting of hydrogen, methyl, ethyl, tert-butyl, methoxy, phenyl, fluorine, chlorine, bromine, trifluoromethyl, hydroxyl, acetoxy, and p-toluenesulfonyloxy;
wherein the sodium perfluoroalkylsulfinate is
wherein the transition metal compound is selected from the group consisting of a copper compound, a cobalt compound, and an iron compound;
wherein the peroxide is hydrogen peroxide or tert-butyl hydroperoxide (TBHP);
and
wherein the perfluoroalkylsulfinate ester has the following chemical structural formula:
n is 1 to 8.

8 more elements

Dependencies are inferred from the claim text.