Some embodiments of the invention include inventive catalysts (e.g., catalysts of Formula (I)). Other embodiments include compositions comprising the inventive catalysts. Some embodiments include methods of using the inventive catalysts (e.g., in hydrofluorination of an organic compound). Further embodiments include methods for making the inventive catalysts. Additional embodiments of the invention are also discussed herein.

Some embodiments of the invention include inventive catalysts (e.g., catalysts of Formula (I)). Other embodiments include compositions comprising the inventive catalysts. Some embodiments include methods of using the inventive catalysts (e.g., in hydrofluorination of an organic compound). Further embodiments include methods for making the inventive catalysts. Additional embodiments of the invention are also discussed herein.

A method for producing at least one olefin compound selected from the group consisting of a compound of formula (51) and a compound of formula (52), the method including reacting an olefin compound of formula (21) with a olefin compound of formula (31) in the presence of at least one metal catalyst selected from the group consisting of a compound of formula (11), a compound of formula (12), a compound of formula (13), a compound of formula (14), and a compound of formula (15).

##STR00001##

A method for producing at least one olefin compound selected from the group consisting of a compound of formula (51) and a compound of formula (52), the method including reacting an olefin compound of formula (21) with a olefin compound of formula (31) in the presence of at least one metal catalyst selected from the group consisting of a compound of formula (11), a compound of formula (12), a compound of formula (13), a compound of formula (14), and a compound of formula (15).

##STR00001##

To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH.sub.2—R.sup.A—CH.sub.2OH, the compound (2) is X.sup.1C(═O)—C(R.sup.B)(R.sup.C)(R.sup.D), R.sup.A is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X.sup.1 is a halogen atom, and —C(R.sup.B)(R.sup.C)(R.sup.D) is a branched group.

To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH.sub.2—R.sup.A—CH.sub.2OH, the compound (2) is X.sup.1C(═O)—C(R.sup.B)(R.sup.C)(R.sup.D), R.sup.A is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X.sup.1 is a halogen atom, and —C(R.sup.B)(R.sup.C)(R.sup.D) is a branched group.

To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH.sub.2—R.sup.A—CH.sub.2OH, the compound (2) is X.sup.1C(═O)—C(R.sup.B)(R.sup.C)(R.sup.D), R.sup.A is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X.sup.1 is a halogen atom, and —C(R.sup.B)(R.sup.C)(R.sup.D) is a branched group.

Object: An object of the present invention is to provide a method for producing, with a high yield, a fluorinated organic compound, the fluorinated organic compound having not been produced with a sufficient yield by a conventional method for producing a fluorinated organic compound using a fluorinating agent containing IF.sub.5-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent. Means for achieving the object: A method for producing a fluorinated organic compound comprising step A of fluorinating an organic compound by bringing the organic compound into contact with (1) IF.sub.5-pyridine-HF and (2) at least one additive selected from the group consisting of amine hydrogen fluorides, X.sup.aF (wherein X.sup.a represents hydrogen, potassium, sodium, or lithium), oxidizers, and reducing agents.

Object: An object of the present invention is to provide a method for producing, with a high yield, a fluorinated organic compound, the fluorinated organic compound having not been produced with a sufficient yield by a conventional method for producing a fluorinated organic compound using a fluorinating agent containing IF.sub.5-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent. Means for achieving the object: A method for producing a fluorinated organic compound comprising step A of fluorinating an organic compound by bringing the organic compound into contact with (1) IF.sub.5-pyridine-HF and (2) at least one additive selected from the group consisting of amine hydrogen fluorides, X.sup.aF (wherein X.sup.a represents hydrogen, potassium, sodium, or lithium), oxidizers, and reducing agents.

Object: An object of the present invention is to provide a method for producing, with a high yield, a fluorinated organic compound, the fluorinated organic compound having not been produced with a sufficient yield by a conventional method for producing a fluorinated organic compound using a fluorinating agent containing IF.sub.5-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent. Means for achieving the object: A method for producing a fluorinated organic compound comprising step A of fluorinating an organic compound by bringing the organic compound into contact with (1) IF.sub.5-pyridine-HF and (2) at least one additive selected from the group consisting of amine hydrogen fluorides, X.sup.aF (wherein X.sup.a represents hydrogen, potassium, sodium, or lithium), oxidizers, and reducing agents.