Method for producing fluorine-containing olefin

1. A method comprising:

reacting a compound of formula (2) with a compound of formula (7), in the presence of at least one compound selected from the group consisting of a compound of formula (1), a compound of formula (3), a compound of formula (4), a compound of formula (8), and a compound of formula (9) to produce at least one compound selected from the group consisting of a compound of formula (10), a compound of formula (11), a compound of formula (12), and a compound of formula (13):

wherein:

[L] is a ligand;

A 1 to A 6 each independently is a functional group selected from the group consisting of functional group (i), functional group (ii), functional group (iii), and functional group (iv), A 1 and A 2 may bond to each other to form a ring, A 3 and A 4 may bond to each other to form a ring, A 5 and A 6 may bond to each other to form a ring, in the case where one of A 1 and A 2 is a halogen atom, the other is a functional group selected from the group consisting of the functional group (i), the functional group (iii) and the functional group (iv), in the case where one of A 3 and A 4 is a halogen atom, the other is a functional group selected from the group consisting of the functional group (i), the functional group (iii) and the functional group (iv), and in the case where one of A 5 and A 6 is a halogen atom, the other is a functional group selected from the group consisting of the functional group (i), the functional group (iii) and the functional group (iv);

X 1 is a fluorine atom, and

X 2 each independently is a functional group selected from the group consisting of the functional group (i), the functional group (ii), the functional group (v) and the functional group (vi), provided that:

the functional group (i) is a hydrogen atom;

the functional group (ii) is a halogen atom;

the functional group (iii) is a monovalent hydrocarbon group having a carbon number of from 1 to 20;

the functional group (iv) is a monovalent hydrocarbon group having a carbon number of from 1 to 20 and comprising one or more atoms selected from the group consisting of a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom;

the functional group (v) is a functional group selected from the group consisting of an alkyl group having a carbon number of from 1 to 12, an alkoxy group having a carbon number of from 1 to 12, an aryl group having a carbon number of from 5 to 20, an aryloxy group having a carbon number of from 5 to 20, a (per)halogenated alkyl group having a carbon number of from 1 to 12, a (per)halogenated alkoxy group having a carbon number of from 1 to 12, a (per)halogenated aryl group having a carbon number of from 5 to 20, and a (per)halogenated aryloxy group having a carbon number of from 5 to 20; and

the functional group (vi) is the functional group (v) comprising one or more atoms selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom.

2. The method according to claim 1 , wherein the compound of the formula (1) is a ruthenium-carbene complex.

3. The method according to claim 1 , wherein one of A 1 and A 2 is a hydrogen atom, and the other is a functional group selected from the group consisting of the functional group (iii) and the functional group (iv).

4. The method according to claim 1 , wherein the compound of the formula (3) and the compound of the formula (4) are reaction products of the compound of the formula (1) with the compound of the formula (2).

5. The method according to claim 1 , wherein the compound of the formula (8) and the compound of the formula (9) are reaction products of the compound of the formula (3) or the compound of the formula (4) with the compound of the formula (7).

6. The method according to claim 1 , wherein, in the formula (2), X 2 is a hydrogen atom, a fluorine atom, a chlorine atom, or a trifluoromethyl group.

7. The method according to claim 6 , wherein the compound of the formula (2) is tetrafluoroethylene.

8. The method according to claim 1 , wherein the compound the formula (7) is at least one compound selected from the group consisting of ethylene, a monosubstituted olefin and a 1,2-disubstituted olefin.

9. The method according to claim 1 , wherein the compound of formula (7) is at least one compound selected from the group consisting of a monosubstituted olefin and a 1,2-disubstituted olefin selected from the group consisting of the functional group (iii) and the functional group (iv).

10. The method according to claim 1 , wherein the compound of the formula (7) is a compound comprising a hetero atom at the vinyl position thereof.

11. The method according to claim 1 , comprising bringing the compound of the formula (1) into contact with the compound of the formula (2) to thereby convert into at least one of the compound of the formula (3) and the compound of the formula (4), and then bringing the converted compound into contact with the compound of the formula (7).

12. The method according to claim 1 , comprising bringing at least one of the compound of the formula (3) and the compound of the formula (4) into contact with the compound of the formula (7) to thereby convert into at least one of the compound of the formula (8) and the compound of the formula (9), and then bringing the converted compound into contact with the compound of the formula (2).

13. The method according to claim 1 , comprising bringing at least one of the compound of the formula (8) and the compound of the formula (9) into contact with the compound of the formula (2) to thereby convert into at least one of the compound of the formula (3) and the compound of the formula (4), and then bringing the converted compound into contact with the compound of the formula (7).

14. The method according to claim 1 , wherein the compound of the formula (2) and the compound of the formula (7) are brought into contact with the compound of the formula (1) simultaneously.

15. The method according to claim 1 , wherein the reaction of the compound of formula (2) with the compound of formula (7) forms a 1,1-difluoro-2-substituted olefin.

16. The method according to claim 1 , wherein the reacting is carried out in a solvent.

17. The method according to claim 1 , wherein at least one of A 3 , A 4 , A 5 , and A 6 is an alkoxy group.

18. The method according to claim 1 , wherein at least one of A 3 and A 4 is of formula —O(CH 2 ) 3 CH 3 .

19. The method according to claim 1 , wherein the compound of formula (7) is an alkyl vinyl ether.

20. The method according to claim 1 , wherein the compound of formula (7) is β-alkoxy styrene.

21. The method according to claim 1 , wherein the compound of formula (7) is an alkyl vinyl ether having an alkyl group with from 4 to 12 carbon atoms.

22. The method according to claim 1 , wherein the compound of formula (2) is at least one selected from the group consisting of tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene and trifluoroethylene.

23. The method according to claim 1 , wherein the compound of formula (2) is at least one of:

wherein ORF is a (per)halogenated alkoxy group having a carbon number of from 1 to 12, or a (per)halogenated alkoxy group having a carbon number of from 1 to 12 and having an etheric oxygen atom between the carbon atom and the carbon atom.