Method for aromatic fluorination
Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO 2 F 2 to a reaction mixture; reacting the SO 2 F 2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO 2 F 2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO 2 F 2 , the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.
1. A fluorination method comprising:
providing a salt having the following structure to a reaction mixture:
where Ar is an aryl or heteroaryl;
where M is a cation;
providing SO 2 F 2 to the reaction mixture;
reacting the SO 2 F 2 and the ammonium salt to provide a fluorinated aryl species having the following structure:
Ar—F.
2. A method according to claim 1 , further comprising providing a solvent to the reaction mixture.
3. The fluorination method of claim 2 , wherein the solvent is selected from the group consisting of polar aprotic solvents, alkoxy ether solvents, nitrile solvents, and aromatic solvents, or a mixture thereof.
4. The fluorination method of claim 1 , wherein the cation is selected from the group consisting of, sodium, potassium, cesium, tetramethylammonium, and tetrabutylammonium.
5. The fluorination method of claim 3 , wherein the cation is selected from the group consisting of, sodium, potassium, cesium, tetramethylammonium, and tetrabutylammonium.
6. A method according to claim 1 , wherein
is tetramethylammonium 4-cyanophenolate.
7. A method according to claim 2 , wherein the solvent comprises a polar aprotic solvent.
8. A method according to claim 2 , wherein the solvent comprises an alkoxy ether solvent.
9. A method according to claim 2 , wherein the solvent comprises a nitrile solvent.
10. A method according to claim 2 , wherein the solvent comprises an aromatic solvent.
11. A method according to claim 3 , wherein the cation is sodium.
12. A method according to claim 3 , wherein the cation is potassium.
13. A method according to claim 3 , wherein the cation is cesium.
14. A method according to claim 3 , wherein the cation is tetramethylammonium.
15. A method according to claim 3 , wherein the cation is tetrabutylammonium.
16. A method according to claim 2 , wherein the solvent comprises dimethyl formamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, dimethylacetamide, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, dichloromethane, acetonitrile, ethyl acetate, hexamethylphosphoric triamide, or 1,3-dimethyl-2-imidazolidinone.
17. A method according to claim 2 , wherein the solvent comprises DMF.
18. A method according to claim 2 , wherein the solvent comprises tetrahydrofuran, diglyme, or dimethoxyethane.
19. A method according to claim 2 , wherein the solvent comprises benzonitrile.
20. A method according to claim 2 , wherein the solvent comprises toluene.