Method for producing fluorine-containing olefin compound

1. A method for producing at least one compound of a fluorine-containing olefin compound of formula (51) or a fluorine-containing olefin compound of formula (52), the method comprising:

reacting a fluorine-containing olefin compound of formula (21) with an olefin compound of formula (31) to form the fluorine-containing olefin compound of formula (51) or the fluorine-containing olefin compound of formula (52);

wherein the reaction is carried out in the presence of a metal-carbene complex compound (10) having an olefin metathesis reaction activity and a compound of formula (41), or in the presence of the metal-carbene complex compound (10) and an olefin compound of formula (42):

wherein A 11 and A 12 are each independently a group selected from the group consisting of group (i), group (iia), group (iii), and group (iv), and A 11 and A 12 may bond to each other to form a ring;

with the proviso that in the case where one of A 11 or A 12 is a halogen atom, the other is a group selected from the group consisting of group (i), group (iii), and group (iv);

A 13 is a group selected from the group consisting of the following group (i), group (iii), and group (iv);

E is a group selected from the group consisting of —OR′, —OSiR′ 3 , —NR′ 2 , —SR′, and group (iia), and each R′ is independently a group selected from the group consisting of group (i), group (v), and group (vi);

A 13 and E may bond to each other to form a ring;

X 11 and X 12 are each independently a group selected from the group consisting of group (i), group (ii), group (v), and group (vi), and X 11 and X 12 may bond to each other to form a ring;

X 13 is a group selected from the group consisting of group (ii), group (v), and group (vi);

R 11 to R 14 are each independently a group selected from the group consisting of —H, —CH 2 R, —CH(CR 3 ) 2 , —C(CR 3 ) 3 , and —Ar,

wherein each R is independently a group selected from the group consisting of a hydrogen atom, an alkyl group having a carbon number of from 1 to 12, and an alkyl group having a carbon number of from 1 to 12 and having an etheric oxygen atom between carbon atoms, and Ar is an aryl group having a carbon number of from 5 to 12;

R 11 and R 12 may bond to each other to form a ring;

R 13 and R 14 may bond to each other to form a ring;

group (i): a hydrogen atom;

group (ii): a halogen atom;

group (iia): a chlorine atom, a bromine atom, or an iodine atom;

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

group (iv): a monovalent hydrocarbon group having a carbon number of from 1 to 20 and containing 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;

group (v): a 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;

group (vi): the group (v) further containing 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 production method according to claim 1 , wherein the olefin compound of formula (41) or formula (42) is at least one compound selected from the group consisting of

wherein each R′ is independently a group selected from the group consisting of group (i), group (v), and group (vi).

3. The production method according to claim 1 , wherein X 13 in the fluorine-containing olefin compound of formula (21) is a halogen atom or a perhalogenated alkyl group having a carbon number of from 1 to 8.

4. The production method according to claim 1 , wherein a metal in the metal-carbene complex compound (10) is ruthenium, molybdenum, or tungsten.

5. The production method according to claim 1 , wherein a metal in the metal-carbene complex compound (10) is ruthenium.

6. The production method according to claim 1 , wherein a metal in the metal-carbene complex compound (10) is molybdenum or tungsten and the metal-carbene complex compound (10) has an imide ligand and a ligand including two coordinating oxygen atoms as a ligand [L].

7. The production method according to claim 1 , wherein in the olefin compound of formula (21), X 11 is group (i), group (ii), group (v), or group (vi), X 12 is group (i), group (ii), group (v), or group (vi), and X 13 is group (ii), group (v) or group (vi).

8. The production method according to claim 1 , wherein the olefin compound of formula (21) is a 1,1-difluoroolefin.

9. The production method according to claim 1 , wherein the olefin compound of formula (21) is at least one olefin compound selected from the group consisting of

wherein Rf is a (per)fluorinated alkyl group having a carbon number of from 1 to 20, a (per)fluorinated alkyl group having a carbon number of from 1 to 20 and having an etheric oxygen atom between a carbon atom and a carbon atom, or a (per)fluorinated aryl group having a carbon number of from 5 to 20.

10. The production method according to claim 1 , wherein the reaction is carried out at a temperature of from 0 to 150° C.

11. The production method according to claim 1 , wherein the reaction is carried out in the absence of a solvent.

12. The production method according to claim 1 , wherein the metal of the metal-carbene complex compound (10) is molybdenum or tungsten and the metal-carbene complex compound (10) has an imide ligand of formula ═NR 1 where R 1 is an alkyl or aryl group.

13. The production method according to claim 1 , wherein the metal-carbene complex compound (10) is at least one selected from the group consisting of

14. The production method according to claim 1 , wherein the metal-carbene complex compound (10) has the following formula

wherein A 1 and A 2 are each independently a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having a carbon number of from 1 to 20, or a monovalent hydrocarbon group having a carbon number of from 1 to 20 and containing 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, wherein A 1 and A 2 may bond, as a divalent group formed by removing one hydrogen or halogen atom, to each other to form a ring.