A production method of producing a fluorine-containing olefin by allowing a first olefin represented by the following Formula (1) and a second olefin to react with each other in the presence of a ruthenium compound represented by the following Formula (X) is provided.

##STR00001##

A production method of producing a fluorine-containing olefin by allowing a first olefin represented by the following Formula (1) and a second olefin to react with each other in the presence of a ruthenium compound represented by the following Formula (X) is provided.

##STR00001##

A production method of producing a fluorine-containing olefin by allowing a first olefin represented by the following Formula (1) and a second olefin to react with each other in the presence of a ruthenium compound represented by the following Formula (X) is provided.

##STR00001##

The present invention relates to a transition metal complex having a PNNP4 ligand, which is easy to manufacture and handle and is relatively inexpensively available, and a method for manufacturing the same, as well as a method using this transition metal complex as a catalyst for hydrogenation reduction of ketones, esters and amides to manufacture corresponding alcohols, aldehydes, hemiacetals and hemiaminals, a method using this transition metal complex as a catalyst for oxidation of alcohols, hemiacetals and hemiaminals to manufacture corresponding carbonyl compounds, and a method using this transition metal complex as a catalyst for dehydrogenation condensation between alcohols and amines to manufacture alkylamines.

The present invention relates to a transition metal complex having a PNNP4 ligand, which is easy to manufacture and handle and is relatively inexpensively available, and a method for manufacturing the same, as well as a method using this transition metal complex as a catalyst for hydrogenation reduction of ketones, esters and amides to manufacture corresponding alcohols, aldehydes, hemiacetals and hemiaminals, a method using this transition metal complex as a catalyst for oxidation of alcohols, hemiacetals and hemiaminals to manufacture corresponding carbonyl compounds, and a method using this transition metal complex as a catalyst for dehydrogenation condensation between alcohols and amines to manufacture alkylamines.

Disclosed are a salt represented by formula (I), and a method for producing the salt, and a quencher and a resist composition comprising the same: ##STR00001## wherein R.sup.1 and R.sup.2 each represent a hydrocarbon group, and —CH.sub.2— included in the hydrocarbon group may be replaced by —O— or —CO—; R.sup.3, R.sup.4 and R.sup.5 each represent a halogen atom, an alkyl fluoride group or a hydrocarbon group, and —CH.sub.2— included in the hydrocarbon group may be replaced by —O— or —CO—; m3 represents an integer of 0 to 2, and when m3 is 2, two R.sup.3 may be the same or different from each other; and m4 and m5 represent an integer of 0 to 5, and when m4 and/or m5 is/are 2 or more, a plurality of R.sup.4 and/or a plurality of R.sup.5 may be the same or different from each other.

The present invention aims to provide a method by which fluorine-containing sulfide compounds, particularly sulfide compounds that contain hydrogen and fluorine, can be produced in a simple, low-cost and industrial manner. Provided is a method of producing a fluorine-containing sulfide compound represented by the following formula (2):
(F).sub.n-A.sup.3-S-A.sup.4-(F).sub.m  (2)
(wherein A.sup.3 and A.sup.4 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of fluorine atoms binding to A.sup.3 and A.sup.4, with n+m=1 to 13 being satisfied), comprising reacting a chlorine-containing sulfide compound represented by the following formula (1):
(Cl).sub.n-A.sup.1-S-A.sup.2-(Cl).sub.m  (1)
(wherein A.sup.1 and A.sup.2 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of chlorine atoms binding to A.sup.1 and A.sup.2, with n+m=1 to 13 being satisfied) and a fluorinating agent.

The present invention aims to provide a method by which fluorine-containing sulfide compounds, particularly sulfide compounds that contain hydrogen and fluorine, can be produced in a simple, low-cost and industrial manner. Provided is a method of producing a fluorine-containing sulfide compound represented by the following formula (2):
(F).sub.n-A.sup.3-S-A.sup.4-(F).sub.m  (2)
(wherein A.sup.3 and A.sup.4 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of fluorine atoms binding to A.sup.3 and A.sup.4, with n+m=1 to 13 being satisfied), comprising reacting a chlorine-containing sulfide compound represented by the following formula (1):
(Cl).sub.n-A.sup.1-S-A.sup.2-(Cl).sub.m  (1)
(wherein A.sup.1 and A.sup.2 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of chlorine atoms binding to A.sup.1 and A.sup.2, with n+m=1 to 13 being satisfied) and a fluorinating agent.

The present invention aims to provide a method by which fluorine-containing sulfide compounds, particularly sulfide compounds that contain hydrogen and fluorine, can be produced in a simple, low-cost and industrial manner. Provided is a method of producing a fluorine-containing sulfide compound represented by the following formula (2):
(F).sub.n-A.sup.3-S-A.sup.4-(F).sub.m  (2)
(wherein A.sup.3 and A.sup.4 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of fluorine atoms binding to A.sup.3 and A.sup.4, with n+m=1 to 13 being satisfied), comprising reacting a chlorine-containing sulfide compound represented by the following formula (1):
(Cl).sub.n-A.sup.1-S-A.sup.2-(Cl).sub.m  (1)
(wherein A.sup.1 and A.sup.2 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of chlorine atoms binding to A.sup.1 and A.sup.2, with n+m=1 to 13 being satisfied) and a fluorinating agent.

Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. For example, methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.