An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

A living radical polymerization initiator represented by the following:

##STR00001##

wherein, R.sup.1 represents an aromatic, an alkylcarbonyl, an alkoxycarbonyl, an aminocarbonyl, an alkylaminocarbonyl, a dialkylaminocarbonyl, an arylcarbonyl, an alkylsulfonyl, an aryl sulfonyl or combinations thereof; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are a hydrogen, an aliphatic, an aromatic, an alkylcarbonyl, an alkoxycarbonyl, an aminocarbonyl, an alkylaminocarbonyl, a dialkylaminocarbonyl, an arylcarbonyl, a carboxy, an alkylsulfonyl or an aryl sulfonyl; X and Y are a halogen; m and n are an integer of 1 or more, and

##STR00002## are non-symmetrical so that X and Y have different reactivities to initiate a living radical polymerization.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

An object of the present invention is to provide a process for producing α-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): ##STR00001##
wherein R.sup.1 and R.sup.2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R.sup.3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): ##STR00002##
wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3):
R.sup.3—OH  (3)
wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).

An object of the present invention is to provide a process for producing α-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): ##STR00001##
wherein R.sup.1 and R.sup.2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R.sup.3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): ##STR00002##
wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3):
R.sup.3—OH  (3)
wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.