Perfluoroalkylation of carbonyl compounds

1. A process for producing a compound comprising a perfluorinated alkyl group moiety from a carbonyl compound, said process comprising contacting a carbonyl compound with a silane compound comprising a perfluoroalkyl group in the presence of a fluorohydrogenate ionic liquid under conditions sufficient to produce a compound comprising a perfluorinated alkyl group, wherein the amount of said fluorohydrogenate ionic liquid used in the process is less than 1 equivalent relative to the amount of said carbonyl compound.

2. The process of claim 1 , wherein said carbonyl compound is an aldehyde, a ketone, or an ester.

3. The process of claim 1 , wherein said silane compound is a perfluoroalkyl(trialkyl)silane compound.

4. The process of claim 1 , wherein said fluorohydrogenate ionic liquid comprises a quaternary ammonium cation.

5. The process of claim 4 , wherein said quaternary ammonium cation comprises a nitrogen-heteroaryl cation.

6. The process of claim 4 , wherein said quaternary ammonium cation comprises N-ethyl-N-methylimidazolium, N-methyl-N-propylpyrrolidinium, N-methyl-N-butylpyrrolidinium or a combination thereof.

7. A process for producing a siloxy compound of the formula:

comprising contacting a carbonyl compound of the formula:

with a silyl compound of the formula:

(R 3 ) 3 Si(C n F 2n+1 )  III

in the presence of a fluorohydrogenate ionic liquid under conditions sufficient to produce a siloxy compound of Formula I,

wherein

n is an integer from 1 to 30;

R 1 is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, heteroalkyl, (cycloalkyl)alkyl, (heterocycloalkyl)alkyl, aralkyl or heteroaralkyl;

R 2 is hydrogen, alkyl or a moiety of the formula —OR 4 , wherein R 4 is alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, heteroalkyl, (cycloalkyl)alkyl, (heterocycloalkyl)alkyl, aralkyl or heteroaralkyl; and

each of R 3 is independently alkyl, cycloalkyl, aryl, (cycloalkyl)alkyl or aralkyl, and wherein the amount of said fluorohydrogenate ionic liquid used in the process is less than 1 equivalent relative to the amount of said carbonyl compound of Formula II.

8. The process of claim 7 , wherein R 2 is a moiety of the formula —OR 4 , wherein R 4 is alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, heteroalkyl, (cycloalkyl)alkyl, (heterocycloalkyl)alkyl, aralkyl or heteroaralkyl.

9. The process of claim 8 further comprising the step of hydrolyzing said siloxy compound of Formula I to produce a ketone compound of the formula:

wherein n is an integer from 1 to 30.

10. The process of claim 7 , wherein each of R 3 is independently C 1 -C 6 alkyl.

11. The process of claim 10 , wherein R 3 is methyl.

12. The process of claim 7 , wherein said fluorohydrogenate ionic liquid comprises a quaternary ammonium cation.

13. The process of claim 12 , wherein said quaternary ammonium cation comprises a nitrogen-heteroaryl cation.

14. The process of claim 13 , wherein said quaternary ammonium cation comprises N-ethyl-N-methylimidazolium, N-methyl-N-propylpyrrolidinium, N-methyl-N-butylpyrrolidinium or a combination thereof.

15. The process of claim 7 , wherein R 2 is hydrogen or alkyl.

16. The process of claim 15 further comprising the steps of hydrolyzing said siloxy compound of Formula I to produce an alcohol compound of the formula:

17. The process of claim 7 , wherein the amount of said fluorohydrogenate ionic liquid used in the process ranges from about 0.2 to 0.4 equivalent relative to the amount of said carbonyl compound of Formula II.

18. The process of claim 7 , wherein the amount of said silyl compound of Formula III used in the process is at least 1 equivalent relative to the amount of said carbonyl compound of Formula II.